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Ultimate Art Lover’s New England Road Trip

By Robert Firpo-Cappiello
October 27, 2017
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It’s no surprise that southern Vermont and western Massachusetts are home to beautiful mountains and woodlands. But you will be delighted to discover that the hills are also alive with peerless paintings and sculpture.

Each time my family drives into Bennington, Vermont, it feels a little like coming home. Though I’ve never lived in this little town for more than a few days at a time on vacation, it strikes a deep, familiar chord with me. Perhaps arriving in Bennington feels like home to me because, as a boy growing up in the Bronx, I recall vividly my first discovery of the great American painter Anna Mary Robertson, better known as Grandma Moses, who lived and worked in Bennington. The gentle curves of the Green Mountains just outside of town provide a soothing natural backdrop to this historic place, and they are the very mountains that appear in Grandma Moses’s folk paintings, depicting rural life and seasonal rituals such as sugar-mapling and trick-or-treating. The interplay between the natural world and the art world is at the very heart of this short and totally manageable road trip.

DAY 1: BENNINGTON, VERMONT

Bennington offers a range of accommodations, but we’ve become fond of the family-friendly Knotty Pine Motel, which has a dog-friendly policy, a very attentive and helpful staff, and a lovely swing set and pool. We especially appreciate the big map of New England that hangs in the main office. My youngest daughter kept asking to go visit the map, and I was so pleased that she’d connected with New England, tracing her finger over my sister’s home in New Hampshire, the beaches of Falmouth and Nantucket where we’ve visited, and the charming little city of New Bedford. It was only later that I realized that my daughter was actually less interested in the map and much more interested in the bowl of Tootsie Rolls the motel proprietor kept on her desk. Oh, well. The map is still a sweet memory, even if the candy was sweeter.

In Bennington, the must-see for art lovers is the Bennington Museum and Grandma Moses Schoolhouse. Here, you can view a wide variety of art in a charming and manageable setting. The museum’s permanent collection includes fine art, furniture, and household items from Vermont’s history as well as strikingly modern work by contemporary Bennington artists. The rooms devoted to Grandma Moses (the largest public collection of the “primitive” artist’s work) offer you the chance to see the Green Mountains in Moses’s iconic paintings or rural life and then peek out the window and see the real thing. Unforgettable.

The adjoining one-room Grandma Moses Schoolhouse includes chalk-boards and antique schoolbooks, games, and dress-up clothes. If you’re traveling with kids, they may be more enthralled by the schoolhouse than the art, and that’s fine: Let them go. They’ll remember how that schoolhouse made them feel long after they’ve forgotten your lectures on folk art.

In 1777, Bennington was the site of a major Revolutionary War battle, and each August, the town celebrates with a parade. Residents and visitors alike line the streets and cheer for the bands and marchers. We’ve been lucky enough to time our visits to parade weekend, and it is a nice way to meet the town’s year-round residents.

Don’t be fooled by the name. Kevin’s Sports Pub and Restaurant, in North Bennington, is much more than a place to watch a game on TV. We love its imaginative riffs on burgers, fish and chips, and other pub fare, and the local ales on tap offer a variety of vibrant flavors and textures.

In nearby South Shaftsbury, the Robert Frost Stone House Museum surprises, delights, and educates visitors with Frost’s famous poetry, such as “The Road Not Taken,” adorning the walls, with brief, easily digested lessons on his rhyme schemes and meter that even young kids will understand and appreciate. (If you’re headed for the Atlantic coast, drop by another Frost museum, his farmhouse in Derry, New Hampshire, on the way.)

Psst! Outside Bennington, there’s a hidden gem of a local lake whose name I promised not to publish because its modest snack bar and canoe rental business are really meant for locals. If you find yourself in conversation with a Bennington local, do ask about places to canoe. We had a family paddling adventure on the lake and down a nearby creek that we’ll never forget.

DAY 2: WILLIAMSTOWN, MASSACHUSETTS

Williamstown, just across the border into Massachusetts down U.S. 7, is another town where you can easily stay more than one night just to drink in all the art and natural beauty on display. The Clark Art Institute is home not only to a world-class permanent collection that includes European and American art from the Renaissance to the early 20th century (especially rich in work by American painters Winslow Homer, George Inness, and John Singer Sargent), but also to one of the finest museum snack bars I’ve ever experienced. For real. I recommend its salads and sandwiches, especially in good weather when you can eat out on a terrace. The museum’s grounds, including a children’s learning center, are a work of art themselves (they made Architectural Digest’s list of “buzz-worthy” museums). Williams College Museum of Art is another fine collection; focused on the college’s mission, the museum offers a broad range of pieces, from ancient Egyptian art to contemporary American and international work.

Williamstown Theatre Festival has been bringing acclaimed productions to the Berkshires each summer since 1955, another example of the exciting synergy between the natural world and human creativity that makes this region so special.

Williams Inn is a cozy place in the heart of Williamstown to rest your head in the Berkshires, having welcomed visitors since 1909. As with Bennington before it, you may want to stay more than one night to see all the sights.

DAY 3: NORTH ADAMS, MASSACHUSETTS

The cherry on top of your art lover’s road trip is the Massachusetts Museum of Contemporary Art (MASS MoCA), in North Adams. The nearby mountains and small-town vibe on the streets are a contrast to the hot, ultra-modern work you’ll encounter inside this restored 19th-century mill complex. The museum is an epicenter for the making of visual and performing arts, with residencies that bring cutting-edge creators to town. New exhibits of contemporary artists, including the museum’s Kidspace, are ongoing; check the museum’s excellent website, massmoca.org, for updates. When you’re ready to refuel, MASS MoCA’s Lickety Split lobby bistro is open during museum hours for breakfast and lunch (plus ice cream, espresso, fresh-squeezed lemonade, and, on show nights, a light dinner menu). The cute streets of North Adams also teem with international cuisine, funky cafés and coffee spots, and cool pubs. 

Ready to hit the hay? The Porches Inn at MASS MoCA is self-consciously kitschy. (In keeping with the museum’s mission, the inn describes itself as “retro-edgy, industrial granny chic.”) You’ll enjoy closing your little hipster eyes in the imaginative heart of the Berkshires.

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Road Trips

12 Best Fall Foliage Trips

It's the most colorful time of the year! Here in the northeast, we're surrounded by beautiful shades of orange, red, and yellow as leaf-peeping season kicks into full swing—but you don't have to be in just one region to appreciate all the fall foliage. We've got 11 great seasonal spots around the country—and one in eastern Canada—where you can see the leaves in all their colorful splendor, whether by car, train, boat, or by going for a nice, long walk in the crisp fall air. If all else fails, you can always choose to live vicariously through our Fall Into Foliage board on Pinterest. SEE YOUR BEST PHOTOS OF BEAUTIFUL FALL COLORS! 1. VERMONT It goes without saying that Vermont is one of the most well-known places in the U.S. when it comes to fall foliage—especially in the central and southern parts of the state, the Lake Champlain Islands, areas near Burlington, and in the beautiful Green Mountains. As of right now, most of the state is already seeing the first hint of fall colors, with late, more subtle changes in color still slated to happen over the weekends of October. Up for a scenic fall foliage drive? Vermont's Tourism website offers a printable list of more than 20 drives around the state ranging anywhere from 30 to 210 miles long, as well as regional and historical points of interest, apple orchards, and popular local attractions you shouldn't miss along the way. WHERE TO STAY Eddington House Inn, an adorable B&B located in Bennington, Vermont. Rates from $159 per night thru Oct. (from $139 per night Nov. thru June), include complimentary WiFi, breakfast, parking, and sweet treats like locally made chocolate truffles. 2. NEW YORK Whether you're planning to venture upstate in search of fall fun or opt to stay in the big city, New York gives you plenty of options—visit this website for a detailed list of all the great spots within the state to view fall foliage as peak levels tend to change depending on where you are. Baseball fans will want to visit Cooperstown, home to the National Baseball Hall of Fame, while other outdoorsy leaf-peeping activities include renting kayaks on Lake Otsego or hiking among the gorgeous fall colors at Glimmerglass State Park. For an exciting day trip, bring the family to Barton Orchards now through Nov. 2nd, located about a 90-minute drive north of the City in Poughquag, New York, and home to hayrides, train rides, a corn maze, haunted house, and the chance to pick perfect farm-fresh apples, pumpkins, corn and other seasonal vegetables to take home as delicious fall souvenirs. Don't miss the Farm Bakery & Market where you can pick up maple syrup, seasonal mixes and spices, baked pies and desserts, fudge, and best of all, cider donuts. (Activity wristbands are available for $12.50 and include a $3 general admission fee. Prices for fresh-picked apples, pumpkins, and veggies vary by quantity. Please note that no outside food or beverages are allowed on the farm, but feel free to bring your own wagon). Or if you'd rather stay in the heart of the Big Apple, go for a stroll around Central Park, Prospect Park in Brooklyn, or Pelham Bay Park in the Bronx in the fall for vibrant color changes during the last few weeks of October into November—pick any spot in the park for a fall picnic, just don't forget to bring your camera! WHERE TO STAY The Wyndham New Yorker Hotel has a great vacation package now thru Dec. 29, 2015, that includes overnight accommodations from $169 per night, continental breakfast, and free tickets to the Empire State Building. 3. CANADA While there are definitely enough places in Canada to warrant its own fall foliage report, we'd like to point out one of our favorite spots in Québec for the purposes of this story: Mont Tremblant, an exquisite ski town roughly two hours outside of Montréal that always has something fun going on no matter what season we're in, and fall is no exception. Hop a quick flight on Porter Airlines from Newark, Washington D.C., Burlington, Chicago, Myrtle Beach, or from any of 12 connecting Canadian cities to reach this beautiful ski town nestled in the heart of Canada's Laurentians (they even serve wine onboard—for free!). In Tremblant, there are plenty of outdoor activities to keep you busy while you're admiring the fall colors showcased on the mountains around you: play a round of golf on one of the area's two championship golf courses, treat youself to a 60-minute cruise on the 7.5-mile long Lake Tremblant ($24 for adults; $19 for seniors ages 60 and up; $8 for children ages 2-12, free for children two and under), rent a bike for the afternoon (prices vary), explore the mountain on one of 12 hiking trails, or take a ride to the summit on the panoramic gondola (Adults pay $19.99 per ride; children ages 6-12 pay $15.99; children ages 3-5 pay $4.19, and those under age 2 ride for free; Gondola tickets must be purchased online at least two days in advance). After a long day outside, try your luck at the Casino de Mont-Tremblant (a free shuttle is available every 30 minutes between the casino and the pedestrian village), relax your tired muscles at the nearby Scandinave Spa Mont-Tremblant (access to the Scandinavian Baths for $48 per person; 60-minute Swedish Massages from $130 per person including access to the baths. Take advantage of their fall special—$35 Scandinavian Bath access or $95 for a 60-minute massage with baths), or check out one of the special fall sales happening at Tremblant's many boutique shops. WHERE TO STAY The Residence Inn Mont Tremblant Manoir Labelle offers rooms from $157 per night and is within walking distance of most area attractions. 4. COLORADO Estes Park is the perfect place to view not only fall foliage, but also elk and other area wildlife this time of year. Nature lovers can go fishing, hiking, mountain biking, and horseback riding in nearby Estes Valley, or even participate in flood recovery efforts. For a spookier fall experience, try one of the Ghost & History Tours at the Historic Stanley Hotel, also known for having paranormal investigators and psychics onsite. Autumn is also the best time of year to take a drive on the Peak to Peak Scenic Byway, one of the prettiest drives in Colorado, if not the whole U.S. Other scenic leaf-peaping hot spots in Colorado include Kebler Pass near Gunnison-Crested Butte, the 236-mile loop of San Juan Skyway, The Grand Mesa Scenic and Historic Byway, Trail Ridge Road, and Rocky Mountain National Park, among 25 scenic and historic byways that typically showcase the state's world-famous golden Aspens. A ride on the Georgetown Loop Railroad is also a memorable way to see the fall colors and learn a little about the area's mining history. (Tickets are from $25.95 for adults; from $18.95 for children ages 3-15). WHERE TO STAY The Rocky Mountain Park Inn offers rooms from $129 per night—their Dine & Dash package includes overnight accommodations with dinner and drinks for two at their restaurant, Longz Bar & Grill, from $110 per night. 5. WEST VIRGINIA Grant County is home to some of the most beautiful fall foliage in the country, and the best way to see it is by train. For one night only, Oct. 16th, the Autumn Splendor Dinner Train will travel through Petersburg, West Virginia, just in time for the red and gold leaves to make their debut. You'll start by sampling local delicacies during a food and wine tasting at the South Side Depot in Petersburg while you wait for your train, and enjoy a West Virginia-made dinner of beef brisket, shrimp, potatoes, green beans, and your choice of homemade chocolate fudge turtle cake or pumpin cheesecake for dessert, all while admiring the view. (Tickets are $60 per person for adults only; reservations required). WHERE TO STAY For a fun vacation option, stay at the Smoke Hole Caverns & Log Cabin Resort located in Spruce Knob Seneca Rocks National Recreation Area near Seneca Rocks, WV. Rates at the Log Motel range from $69-$119 depending on which day you go, while cottages are available from $129 per night. 6. TENNESSEE In Tennessee's southeastern corner about two hours from Nashville lies Chattanooga, the state's fourth-largest city nestled alongside the Tennessee River, and a prime spot for viewing fall foliage. The best part: not only is Chattanooga known for having a teriffic network of hiking, biking, and nature trails, but you also have the unique opportunity to view fall foliage by boat. Enter the Southern Belle Riverboat, sailing several times a day from Pier 2, with dinner cruises, lunch cruises, sunset cruises or 90-minute sightseeing cruises up and down the gorgeous Tennessee River. Prices for their three-hour Fall Leaf Cruise—available daily from Oct. 1st thru Nov. 15th—start at $35.95 for adults and $17.95 for children ages 3-12. WHERE TO STAY Several hotels in Chattanooga are offering fun specials including two-night/three-day packages with tickets to area attractions like Ruby Falls and Rock City Gardens. 7. MISSOURI If you're looking for the ultimate scenic fall drive, Branson and the Ozarks are home to three of the area's best fall foliage driving tours (and one walking/jogging tour) aimed to please any leaf-peeping enthusiast. Stop by the Welcome Center located at Highway 65 and State Highway 248 for free maps and tips about local attractions, then set off on your fall road trip adventure. The first driving tour takes you on a 90-minute loop around Table Rock Lake and Kimberling City, while the second takes you on a 70-minute loop from Downtown Branson around Forsyth and Rockaway Beach. The third, more in-depth fall foliage drive is a four-hour long journey through Bull Shoals, Peel Ferry, and Mark Twain National Forest, while the walking/jogging tour just takes you on a 1.5-mile tour of Branson Landing and Downtown Branson along Lake Taneycomo, home to Main Street Lake Cruises, another fun way to get a unique look at the region's fall colors. (Tickets are from $26.50 per person. Check the website for more details on pricing and scheduling. Must reserve at least 72 hours ahead). WHERE TO STAY Hilton Promenade at Branson Landing offers rates from $129 per night to stay in the heart of town. 8. WISCONSIN One of our favorite places to write about is Door County, a bucolic peninsula between Lake Michigan and Green Bay not only known for its lakes, art, and cherries, but also as a fall foliage viewing destination. Be sure to check the Fall Color Report for the latest leaf-peeping updates. Embrace changing seasons with any number of available outdoor activities ranging from cruises on the lake, horse-drawn wagon rides around town, to even a scenic airplane ride over the area, or stick to golfing, sailing, fishing, horseback riding, sightseeing, and hunting for that perfect antique souvenir to bring back home. The best part about visiting Door County this time of year: all the roadside stands and farmers' markets selling fresh, hot apple cider among other farm fresh produce and wines from local vineyards. WHERE TO STAY The Lodgings at Pioneer Lane in Ephraim, Wisconsin, offers a small suite from $90 per night year-round and your choice of six larger suites from $109-$139 Nov. thru mid-June and from $169-$199 from mid-June thru Oct 31st. 9. TEXAS Located about an hour and 45 minutes outside of San Antonio near the town of Vanderpool is Lost Maples State Natural Area, one of best spots for fall foliage in all of the Lone Star State. Spend some time admiring the colors of nature during a fall hike, camping trip, bird watching adventure or treat yourself to a fall picnic in the park. In this part of the country, the leaves tend to change color closer to early-to-mid-November, so there's still plenty of time to get in on the action—check the Fall Foliage Report, updated weekly from October thru November, just in case. Keep an eye out for vibrant red, orange, and golden colored leaves near Daingerfield, Martin Creek, Lake Bob Sandlin, and Martin Dies Jr. State Park in East Texas, known for its oaks, elms, and sweetgums. You'll also find golden and bright yellow cottonwoods throughout Palo Duro Canyon and Caprock Canyon State Park, as well as rusty-colored leaves that contrast with a swampy, Spanish moss-covered Caddo Lake State Park. WHERE TO STAY Foxfire Cabins in the Vanderpool area offers cozy two-bedroom log cabins from $90 per night. 10. OREGON In the greater Portland and Columbia River area, fall foliage is served up with a side of waterfalls, majestic gardens, dramatic river gorges, and no shortage of local wineries. Take a drive down the scenic Columbia River Highway for views of 900-foot tall cliffs and steep flowing waterfalls overlooking the vast valley. Fall colors can be seen throughout the vineyards of Willamette Valley, where grape vines light up in a variety of reds and yellows. Hiking enthusiasts should make the scenic 1.2-mile, 600-foot ascent to Multnomah Falls for stunning views of the valley below. WHERE TO STAY Comfort Inn Columbia Gorge Gateway offers rates from $85 per night and puts you right in the heart of the action just a 20-minute drive from Multnomah Falls along the scenic Columbia River. 11. CALIFORNIA Yosemite is a wonderful place to celebrate fall and an ideal time of year to visit without having to worry too much about crowds and high hotel prices. Mono County, in California's Eastern Sierra region, is also known for its colorful mix of evergreens, big-leaf maples, Pacific dogwoods, black oaks, and other trees that usually reach their peak colors in mid-to-late October. WHERE TO STAY We love the Yosemite Naitonal Park hotel package from the Holiday Inn Express & Suites Chowchilla—Yosemite Park Area. You'll get overnight accommodations, a park entrance pass valid for seven days for one vehicle full of people, two tickets for the Yosemite Mountain Sugar Pine Railroad steam train, and other perks, from $158 per night. 12. SOUTH DAKOTA Each year the area is draped in color, from the yellow Aspens, elm, ash, and oak trees, to the bright reds of the sumac and maple trees. It's easy to work these scenic drives in as a way of traveling between sites and cities—one of the most scenic, Iron Mountain Road, is a 17-mile road that winds its way through the Black Hills between Mount Rushmore and Custer State Park, both of which are definitely worth visiting in their own rite. Drive the Peter Norbeck National Scenic Byway, another twisting mountain road that features six rock tunnels and views of the area's mighty Aspens. Hiking and biking enthusiasts can enjoy the 109-mile long Mickelson Trail that runs through the Black Hills with 15 trailheads to choose from. The Spearfish Canyon State & National Forest Service Scenic Byway is also worth a look, as it offers beautiful forest views and all the colors of its spruce, aspen, pine, oak, and birch trees as it winds its way along the Canyon's limestone cliffs. WHERE TO STAY Any of the great hotels mentioned in this story about the perfect South Dakota road trip, including Frontier Cabins in Wall (near Badlands National Park, from $74 per night), Springhill Suites by Marriott in Deadwood (from $79 per night), State Game Lodge in Custer State Park (from $115 per night), or the Adoba EcoHotel Rapid City (from $101 per night).

Road TripsTravel Tips

Affordable High-Tech Cars: Your Road Trip BFF

Budget Travel has been celebrating the Great American Road Trip for more than two decades, and while some of our favorite drives (think Utah’s National Parks, New England’s autumn leaves, Michigan’s Upper Peninsula...) remain the same, the vehicles in which Americans hit the road have evolved exponentially. For Budget Travelers like me, who came of age when a car was, well, just a convenient means to get from Point A to Point B, the latest crop of high-tech rides c3an seem a little sci-fi - you’re basically driving a hybrid smartphone/entertainment center that talks. For that reason, we sometimes assume all that technology is out of reach for thrifty shoppers. Nope. A new generation of reasonably priced cars, such as the latest models of the Chevrolet Cruze Diesel, Toyota Yaris, Ford Focus, and Subaru Impreza, offers an array of tech-driven benefits that will transform your next road trip.  Some of the features that are standard or reasonably available in cars under $20,000 include: Wi-Fi. You can enliven your next family road trip by Skyping with family and friends (or co-workers, if you’re into that kind of thing), or downloading music, books, TV,  and movies to your devices while on the move. Interactivity. For those of you who can’t bear to be separated from your phone, texting, and music apps, features such as Apple CarPlay and Android Auto put those apps right on your car’s display screen, allowing you to talk to Siri, Google Maps, and other programs. Mobile App. Some manufacturers offer an app that transforms your phone or tablet into Mission Control for your car. Send driving directions to your vehicle before you get behind the wheel, start or stop your engine, lock or unlock the doors, or check on Wi-Fi settings and diagnostic information ahead of your trip. On top of the interactive features, we’re seeing great fuel efficiency (especially from the Chevy Cruze Diesel), safety features like a rear-view camera for help with parking and rear traffic, and unexpected roominess in smaller cars that allows for all the packing space you need and some elbow room for passengers.

Road TripsTravel Tips

Read This Before You Rent a Car

Despite rising gas prices, 80 percent of U.S. families are planning a road trip this summer, up 10 percent from last year, a recent AAA survey found. But for many people, taking that dream road trip requires renting a car, which can be a stressful, confusing, and expensive process. The rental car industry is notorious for its array of sometimes confusing options for customers. Last year one in five car renters reported problems with their service, according to J.D. Power’s annual North America Rental Car Satisfaction Study. For consumers, the rental car counter can be treacherous. “Rental car agents are paid on commission, so they’re incentivized to try to upsell you for everything,” says Jonathan Weinberg, creator of AutoSlash.com, a service that tracks rental price changes to help get consumers the best deals. “If you ask whether you need something, they’re going to say yes.” Also, since many rental car companies are good at burying fees and surcharges in long rental agreements—you know, the paperwork you barely glance at before signing—the onus is on you to thoroughly research your options. Indeed, “when renting a car, it’s a ‘buyer beware’ transaction,” says Neil Abrams, president of the Abrams Consulting Group, which tracks the rental car industry. Follow these steps to drive down the costs on your next rental car and enjoy a cheaper, happier road trip. Bring your own transponder Going through a toll can bring unexpected fees when you use the rental car company’s transponder (e.g., E-ZPass, SunPass). “It varies by company, but usually you’re going to get charged a convenience fee of $5 a day starting on the first day that you use it,” says Weinberg. In other words, if you’re traveling for a week and go through a toll on the first day, you’ll get charged a $35 fee for the whole week regardless of whether you go through more tolls. READ: "15 Last Minute Weekend Escapes" Thus, you’ll want to use your own transponder on the trip. If you need to buy one, you can do so online or at some convenience stores like Publix, CVS or Walgreens. Don’t prepay for the car Many rental car companies give you the option to prepay for the rental in exchange for a reduced price, but there are some major caveats. For starters, you’re locking yourself into that price point, but rates often drop as the pickup date approaches—potentially below the prepay rate that you accepted earlier. If that happens and you try to re-book for the lower rate, you’ll get slapped with a cancellation fee of about $50, which could effectively negate the amount of money you’d save by rebooking. The good news is you can still reserve a vehicle without paying for it upfront; then, if the rate drops, you simply cancel and rebook. “Renting a car is not like booking a seat on a flight, where you’re stuck with the reservation,” says Mark Mannell, chief executive of CarRentalSavers.com. “There’s no penalty for cancelling and rebooking.” Don’t prepay for gas When you pick up the car, you’re given the option to pay ahead of time for the car company to refill the gas tank when you return the vehicle. However, you’ll save money by refilling the tank yourself for a couple reasons. First, “anything that’s left in the fuel tank that you bought is non-refundable if you opted to prepay for gas,” says Abrams. Also, when you prepay for gas, the rental company charges you the “local market rate” for the fuel but it’s often more expensive than gas stations that are just a few miles away. “Rental car companies aren’t gas stations,” says Abrams. “They provide fuel as an accommodation, and they charge a premium for it.” READ: "25 Most Beautiful Cities in America" To maximize your savings, use the free GasBuddy app (available on iPhone and Android) to find the cheapest station near the airport. When you return the car, take a photo of the fuel gauge in case the rental car company tries to charge you refueling fee later, advises Abrams. Take photos of pre-existing damage Many companies will provide an inspection report when you pick up the car, but you should still take photos of any pre-existing damage. (Many camera phones also let you time stamp pictures.) If there is pre-existing damage, make sure the rental agent records it in the agreement. Also, don’t forget to take photos when you return the car, says Mannell. Don’t automatically buy rental car insurance Insurance through the rental car company can cost up to $50 a day, depending on the plan you select, but you may already be covered through your existing car insurance, homeowner’s insurance, or credit card. Weinberg says most auto insurance policies include coverage for rental cars. Still, it’s good to check with your insurance company or credit card issuer ahead of time to make sure you’re covered. (NerdWallet.com, a credit card comparison website, has compiled a list of which cards include rental car insurance.) Look into renting from an off-airport location Airports often charge rental car companies airport concession fees, which the rental companies then pass on to customers. As a result, daily rates at off-airport stations can be up to $20 or $30 cheaper per day, so it’s wise to survey your options. Just make sure you factor in the cost of a taxi or Uber ride to the off-site location when comparing prices. After all, “if you’ll wind up paying $50 for a taxi, it may not be worth it,” says Abrams. Compare rates at independent agencies Avis, Hertz, and Enterprise are the three largest rental car companies, but there are a number of smaller agencies that offer competitive rates, such as Fox Rent a Car and Advantage. But you may have to make some concessions if you rent from one of these companies. “You’re not usually going to get newer car models at discount agencies,” says Weinberg. Also, a lot of independent agencies don’t have airport locations. One car rental agency you may want to research carefully is Payless. The Better Business Bureau recently issued a nationwide warning to consumers after having received more than 800 complaints about Payless in the past three years. (The BBB has given the company an F rating.) READ: Read This Before You Book a Vacation Rental Redeem discounts for premium memberships Rental car companies offer discounts to members of frequent flier programs and credit card holders; AAA, Costco, and BJ’s also offer members deals on rental cars. These discounts can often be combined with discount codes from the rental car company. For example, a full-size car rental from Hertz at Ronald Reagan National Airport was $281.85 in a recent search, but plugging in a AAA member discount code and a Hertz discount code dropped the rate to $201.90.

Road Trips

Northwest Nirvana in Oregon

DAY 1: Portland to Mt. Hood Maple-bacon-wrapped dates, a fried-egg sandwich, a side of biscuits with huckleberry jam—from the spread in front of us, you’d think my family and I are fueling up for a triathlon. In truth, the only physical activity we have planned between now and lunch is a quick waterfall hike, but we’re at Tasty n Sons, a Portland brunch institution, and when you’re here, you eat (tastynsons.com). Tasty n Sons is our launch point for our road trip from Portland to central Oregon. Our mission: to convince our almost-5-year-old son, Theo, that road trips are the best trips so that he and his younger brother, Baxter—who, for now, follows Theo’s lead in every way—will happily pile into the car anytime we want to explore our country. If we fail? We set ourselves up for years of are we there yet?” pleas from the backseat. As we head east on Highway 84, Darrell talks up our first stop, telling the kids all about Multnomah Falls, a 611-foot-tall waterfall a quick 40 minutes outside of Portland. A secret spot this is not—2.5 million people visit the falls each year—but that doesn’t make it any less spectacular. Theo is appropriately awed when we step out of the car and get our first glimpse. His only disappointment is that we can’t get right up next to the actual water—a sentiment I anticipated, which is why I choose Horsetail Falls as our next stop. There’s not an official count of waterfalls in Oregon, but there are at least 238, and likely more. Horsetail Falls is one of my favorites for a few reasons. For starters, getting there requires a drive along Historic Columbia River Highway, a narrow two-laner covered by a canopy of evergreens. And then there’s the hike in—an easy 15-minute climb of switchbacks that stops you in your tracks with surprise views of the Columbia River Gorge. But the waterfall itself is the real draw. The falls shoot out in the shape of a horsetail, and hikers can walk not just right up to the water but also behind it, thanks to a cave-like overhang in the rocky bluff. On warm summer days, the pool formed by the falls is a playground for swimmers and their dogs, but temps today are in the mid-60s, so we settle for dipping our toes in the chilly waters. By the time we get to Hood River, a small town whose placement on a bend in the Columbia River draws windsurfers from around the world, we’re ready for lunch. Pfriem Family Brewers feels tailor-made for us, with seasonally inspired pub fare—including a children’s menu with more than just mac and cheese—and a corner toy area where kids can play while their parents finish their IPAs and fresh-hop brews (pfriembeer.com). The brewpub is also in the ideal location: right across the street from Hood River Waterfront Park, where the kids’ climbing wall, seesaws, and swimming beach make for the perfect place to work off road-trip energy (hoodriverwaterfront.org). Fed and happy, we wind up Highway 35, a quiet road that leads away from the river to The Gorge White House (thegorgewhitehouse.com). The historic house and farm is on the Fruit Loop, a 35-mile drive in the Hood River Valley dotted with U-pick farms, wineries, and farm stands with views of Mt. Hood in all its glory, all 11,250 feet of it (hoodriverfruitloop.com). Again we’ve anticipated Theo’s reaction: “But can’t we play in the snow?” And so we’re off to Timberline Lodge, the only ski area in North America with year-round skiing (from $260 per night, timberlinelodge.com). As we check in, Theo and Bax are out the back door and falling backward blissfully into the powder. We’ve barely traveled more than 100 miles, but we’re more than happy to have Timberline as our home for the night. It feels exactly how a mountain lodge should: rustic, sturdy, and with three gargantuan fireplaces at the base of the 90-foot stone chimney, cozy. DAY 2: Mt. Hood to Bend We let ourselves linger at Timberline for the morning. The lodge’s Cascade Dining Room can feel a little formal during dinner if you have young kids in tow, but the breakfast buffet is easy and casual. We pile our plates with farm eggs and freshly baked muffins, and then head outside to the Pacific Crest Trail. Depending on which direction you go, the path will take you as far north as Canada or as far south as Mexico, stopping at each border. Today we settle for an easy walk, pausing every two minutes for the kids to “discover” another rock or hunk of moss. The transition from the west side of the Cascades to the east side is always a surprise, even for those of us who’ve made the trip before. In a matter of just a few miles, the lush vegetation and skyscraping evergreens are replaced with a high-desert landscape of sagebrush, juniper, and crackled dry dirt. Tumbleweed bounces across the road as we make our way east on Highway 26. This is the longest stretch of our trip—90 miles from Timberline to Smith Rock State Park—and the kids are itching to run by the time we pull into the park entrance. We’re immediately endeared by the welcome center, an unassuming hunter-green yurt, and we duck in for advice on kid-friendly hikes. The ranger suggests walking along an easy trail that will give us up-close views of Smith Rock, a towering monolith formed from a volcano’s ash explosions a half million years ago. Sure, Smith Rock is especially popular among rock climbers, but this place is for everyone—photographers mesmerized by the golden light on the rock face, families hoping to spot a river otter or golden eagle, mountain bikers looking for an adrenaline rush. We’ve brought a picnic to maximize our outdoor time and avoid wrangling the kids in yet another restaurant. We coax the boys back in the car with the promise of huckleberry ice cream from Juniper Junction, which Darrell and I spotted just outside the park’s entrance on our way in. Ice cream in hand, we set off for Bend, just 25 miles south on Highway 97. I’m not usually one to waste valuable vacation time inside a hotel, but I make an exception at McMenamins Old St. Francis School (from $170 per night, mcmenamins.com/oldstfrancis). The McMenamin brothers are famous in Oregon for two things: being instrumental in pushing through a 1980s Oregon law that allowed breweries to sell their beer on the premises (hence kicking off the region’s craft-brewery craze), and restoring abandoned buildings like schools and churches and turning them into hotels and brewpubs. Old St. Francis School was, just as its name implies, a Catholic school. The McMenamin brothers bought the building in 2000 and turned it into a hotel, keeping so much of the original character you’d swear you need a hall pass when you walk down the long corridor. The big draw, for me at least, is the mosaic-tiled soaking pool. My family and I suit up and climb in. The warm saltwater recharges us, and by the time we get dressed, we’re ready to hit the town. With Mt. Bachelor in the distance and the Deschutes River running through it, Bend feels like the quintessential outdoorsy town. Polar fleece is acceptable attire anywhere you go, gear shops abound, and the town boasts tons of breweries. We’ve heard rave reviews of the beer at Crux Fermentation Project, and when we learn it has an outdoor area with a fire pit and cornhole setup, we’re sold. The kids improvise their own cornhole rules, and Darrell and I actually get a (very) rare20 minutes to talk only to each other. Small victories, but we’ve learned to take them whenever we can. DAY 3: Bend to the Lodge at Suttle Lake The next morning I practically bound out of bed in anticipation of breakfast. We’re going to the original Sparrow Bakery, a tiny spot in the Old Ironworks District that churns out the most incredible pastries (thesparrowbakery.net). The morning is sunny and almost warm, giving us the perfect excuse to sit in the outdoor courtyard and enjoy the bakery’s famous Ocean Rolls, croissant dough rolled in cardamom, vanilla, and sugar and baked to flaky perfection. We’re eager to get to The Lodge at Suttle Lake, almost an hour northwest of Bend along Highway 20. I’ve saved it as our last stop for a couple of reasons. The first is to soak up the property as it is now, a lakefront lodge and series of cabins that feel sweetly unsophisticated. The second is what the place is about to become. The team behind the Ace Hotel Portland recently bought it and are about to relaunch the property as The Suttle Lodge & Boathouse (thesuttlelodge.com). The character I love will remain, but the team will put their fun, design-savvy stamp on it, making it, as they put it, “a relaxed Cascadian forest lodge as imagined by a gently debauched scout.” There will be a beer garden with lawn games, a huge roaring fireplace to gather around for card games and spirit sipping, arts and crafts workshops, and canoe, kayak, and SUP rentals. In other words, summer camp for the whole family. We’ve rented one of the stand-alone cabins for the night, and as we sit on the porch soaking up the fresh air and bright sun, I tell Theo about how we’ll be able to rent boats here on our next trip and ask if he’d want to come back. “Can we make it a road trip?” he asks, and Darrell and I actually high five each other. Mission accomplished.

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