Shenandoah Valley, Va.
107 miles from Washington, D.C.
A collection of 10 independent cities make up the Shenandoah Valley, nestled in the Blue Ridge Mountains, an idyllic watercolor landscape and outdoor adventure haven.
Shenandoah National Park is famous for its outdoor beauty, accessible via both easy and difficult hiking trails, some of which are part of the park's 101 miles of the Appalachian Trail (540/999-3500, nps.gov/shen, $15 per vehicle, $8 per person). The Limberlost Trail takes you past lush mountain laurel; Old Rag Mountain offers panoramic vistas. To refuel, perch in the Pollock Dining Room's taproom at Skyland Resort Lodge and order a Prohibition Punch, featuring local (legal) moonshine ($7.50), and a slice of famous blackberry ice cream pie, made from scratch from the season's harvest (540/999-2212, visitshenandoah.com/dining/skyland-restaurant, Prohibition Punch $7.50, blackberry ice cream pie $6). Not outdoorsy? Stroll through downtown Winchester with a guided tour of the Patsy Cline Historic House, where the country star lived for five years (540/662-5555, celebratingpatsycline.org, $8), or pick your own flowers in the fragrant fields at White Oak Lavender farm in Harrisonburg (540/421-6345, whiteoaklavender.com, tours $5).
WHERE TO STAY Instead of camping out with her hubby FDR in Shenandoah National Park in 1936, Eleanor Roosevelt opted for luxury in Luray: "Franklin, you can rough it if you want, but I'm staying at the Mimslyn," she allegedly told the president. Even today, the property has opulent touches like Doric columns, formal gardens, and fine dining courtesy in the hotel's "upscale Southern" Circa '31 restaurant—necktie recommended (800/296-5105, mimslyninn.com, from $160).
DRIVING TIP I-81 runs the length of the valley and connects large towns like Winchester, Harrisonburg, and Stanton. Consider jumping onto Skyline Drive to take in some of the most beautiful mountain vistas in the U.S.
56 miles from San Francisco
A walkable mecca for wine and food enthusiasts, Yountville offers glasses of big California reds, award-winning bites, and lush Napa Valley scenery that's a refreshing change from San Francisco's cityscapes.
To sample vino, hop the Napa Valley Wine Train that chugs through the heart of town: It serves meals onboard, and visits local wineries for tours (800/427-4124, winetrain.com, from $135). Or go rogue and create your own tasting of five wines at Cornerstone Cellars (707/945-0388, cornerstonecellars.com). Get Michelin-star-quality flavor for less at chef Thomas Keller's Ad Hoc restaurant by partaking in the evening family-style four-course menu (707/944-2487, adhocrestaurant.com, $45); also, make time to walk through Keller's French Laundry Garden, which nurtures fresh vegetables and fruits used at French Laundry and Bouchon Bistro—it's free and open to the public. On a weekend morning, stop by Bouchon Bakery for the somewhat elusive chocolate doughnut—brioche dough filled with decadent chocolate pastry cream and topped with chocolate frosting and chocolate-covered Rice Krispies. But go early (it opens at 7) to score one (707-944-2253, bouchonbakery.com/yountville). Then float above the horizon on a group hot air balloon ride for eight to 12 passengers or take a romantic trip à deux with Napa Valley Balloons (800/253-2224, napavalleyballoons.com, from $210).
WHERE TO STAY For a French country feel, book a room at Maison Fleurie, a B&B with a morning breakfast buffet and complimentary wine, tea, and hors d'oeuvres in the afternoon. Borrow bicycles from the front desk and go for a leisurely ride when you tire of tippling (800/788-0369, maisonfleurienapa.com, from $145).
DRIVING TIP The most direct route from San Francisco is I-80 East, over the Bay Bridge, to Highway 37 West and then Highway 29 through Napa Valley.
New Braunfels, Tex.
175 miles from Houston
If you visit New Braunfels and don't (a) eat German food or (b) get wet, you're doing something wrong. The town is well known for the innovative 65-acre Schlitterbahn Water Park, but its German history, food, and freshwater activities are equally compelling.
Floating down the spring-fed Comal River on giant inflatable "toobs" is essential in New Braunfels. Rent one for the day or take a guided group trip at Rockin 'R' River Rides (830/629-9999, rockinr.com, call for a group trip quote). Quell your post-river appetite with one of 10 types of schnitzel, pan-fried bouletten (meatballs), or classic brats at Friesenhaus, one of the area's specialty German restaurants (830/625-1040, friesenhausnb.com, schnitzel from $15). No German meal is complete without a hearty dessert, so pop into Naegelin's Bakery, "the oldest bakery in Texas, since 1868," for a big hunk of apple streudel—a whole one is more than two feet long (830/625-5722, naegelins.com).
WHERE TO STAY The 30-unit Greune Mansion Inn, right on the Guadalupe River, has a quiet, Victorian feel, with multiple historical buildings broken up into residences that guarantee each guest his or her own entrance and porch. Many of the units have river views (830/629-2641, gruenemansioninn.com, from $190).
DRIVING TIP Take I-10 to I-46, making sure to avoid Houston rush hour if you can help it.
Hood River, Ore.
62 miles from Portland
Orchards, wineries, and outdoor recreation are all hallmarks of this Columbia River Gorge destination.
Taking a drive on the whimsically named Fruit Loop steers you through 35 miles of orchards, vineyards, forests, and farmland (541/386-7697, hoodriverfruitloop.com). Sampling the area's up-and-coming viticulture is another must: Columbia Wine Tours shuttles from two to 24 people to four wineries in four hours and provides bottled waters and snacks along the way (541/380-1410, hoodrivertours.com, two-person tour $140). Or if you prefer hops to grapes, swing by the Full Sail Brewing Company Tasting Room & Pub for a sip (or three) of Full Sail Amber (541/386-2247, fullsailbrewing.com). Dubbed the "windsurfing capital of the world" by some, Hood River is an ideal place to test your mettle on the water: Hood River Waterplay offers five different levels of windsurfing classes, plus equipment rental if you need it (541/386-9463, hoodriverwaterplay.com, from $69).
WHERE TO STAY Seven Oaks Bed and Breakfast describes itself as a "garden oasis," surrounded by two acres of flowering plant life and fenced in by Douglas firs. The four-unit house (plus separate cottage) provides storage for recreational equipment and serves organic eggs, jams, and pastries (541/386-7622, sevenoaksbb.com, $160).
DRIVING TIP I-84—a.k.a. the Columbia River Highway—is a straight, gorgeous shot from Portland. Look for both mountains: Mount Hood and Mount Adams.
Harbor Country, Mich.
26 miles from Chicago
Hitting the beach in the heart of the Midwest is possible at Harbor Country, a group of eight towns on the white-sand beaches of Lake Michigan. The southern beaches of New Buffalo and Warren Dunes State Park are biggest, but individual townships have access too (harborcountry.org).
Charter a fishing boat in the New Buffalo Harbor with Cap'n D Charters to hunt down salmon, trout, bass, and blue gill (574/232-0436, capndcharters.com, $500 for up to four people for six hours) or try surfing or stand-up paddleboarding in New Buffalo or St. Joseph, assisted by Third Coast Surf Shop (269/932-4575, thirdcoastsurfshop.com, $75 for a 90-minute private lesson). Afterward, head to Three Oaks to the brand-new organic Journeyman Distillery, nestled in a former corset-making factory, and kick back in the tasting room for a sample of Featherbone Bourbon, a nod to the turkey feathers that the corsets were fashioned out of (269/820-2050, journeymandistillery.com). Soak up the booze at Skip's in New Buffalo, famous for its ultra-tender prime rib (269/469-3330, skipsrestaurantandcatering.info, from $22).
WHERE TO STAY Directly across the road from its own private beach, the 31-room Lakeside Inn, built in the late 1800s, has a front porch filled with rocking chairs, plus an on-site café (269/469-0600, lakesideinns.com, from $80).
DRIVING TIP Stick to highways 90 or 94. Creatively taking the back roads will only lead you into stop-and-go traffic.
207 miles from Memphis
How to describe Clarksville? "Think Carrie Bradshaw meets Dolly Parton," suggests the Clarksville Chamber of Commerce's website. With entertainment offerings just as diverse as those two pop culture icons, Clarksville manages to be a little bit country, a little bit rock 'n' roll.
The tobacco trade—specifically stemmeries—brought in the big bucks in Clarksville in the late 1800s: Tour the Greek Revival/Italinata-style Smith-Trahern mansion, built in 1958 by a wealthy tobacconist - the slaves' quarters out back are still standing, as is an adjacent 1700s cemetery (931/648-5725, fceclarksville.org, $2). Continue exploring the past via the trails at Fort Defiance Civil War Park, between the Red and Cumberland rivers. The site was a Confederate fort that fell to Union soldiers in 1862; soon after, it served as a safe place for freed and runaway slaves (931/472-3351, fortdefianceclarksville.com). Or, hike one of three trails at Dunbar Cave State Park—the caves were once mined for gunpowder (931/648-5526, tn.gov/environment/parks/dunbarcave). Cool off afterward amid 1870s architecture downtown, at the Blackhorse Pub & Brewery, which makes its own beer onsite, including the signature Barnstormer Red Ale, made with Bavarian Hallertau hops. Pair it with one of the eatery's specialty pizzas, like the Whitehorse, a pie topped with alfredo sauce, fresh spinach, sun-dried tomatoes, artichoke hearts, feta, provolone, and mozzarella (931/552-3726, theblackhorsepub.net, from $15.50).
WHERE TO STAY For an authentic 1800s experience, drive 15 miles southwest of Clarksville to Lylewood Inn Bed & Breakfast in Indian Mound, run by Mandy Williams. The rich antebellum décor—some rooms have claw-foot bathtubs—is matched in decadence only by the group meals: In addition to the requisite country breakfast, home-cooked dinners can include glazed pork loin, garlic cheese biscuits, and fresh berry cobbler (931/232-4203, lylewoodinn.com, from $75).
DRIVING TIP Take Highway 40 to Highway 24, but don't fear the backroads. Visit the Tennessee Trails and Byways website for multiple mapped driving routes from different destinations - like the "Screaming Eagle" trail that begins in Nashville (tntrailsandbyways.com).
Excelsior Springs, Mo.
28 miles from Kansas City, Mo.
Soak up the late-18th and early-19th century history of Excelsior Springs, a Missouri town that boomed due to its wealth of pure, natural springwater. Early tourists came from miles around to bathe in the mineral-rich H2O and hopefully heal their ailments, and the city has preserved that craze via historic buildings and walking tours.
Belly up to the world's longest water bar, housed in the Art Deco-style Hall of Waters and Cultural Museum, built in 1937, where you can taste the mineral waters that put Excelsior Springs on the map (816/637-2811, visitesprings.com). A few blocks down, stop into Oooey Gooey Chocolates for a chocolate-dipped Twinkie on a stick—your choice of either milk or white chocolate (816/630-9255, oooeygooey.com, $2.25). Or get away from it all at the 40-acre Knott Nature Sanctuary, which features education and recreation programs that include hiking, camping, and gardening and landscaping (816/630-2872).
WHERE TO STAY Notorious characters Al Capone and Bugsy Malone reportedly threw their own bathtub gin and gambling parties at The Elms Resort and Spa, which reopened this year for its 100th anniversary after a multi-million-dollar renovation that includes a spa with a hydrotherapy grotto. The hotel is perhaps best known, though, for being the place Harry S. Truman found out he'd defeated Dewey for the presidency in 1948 (816/630-5500, elmshotelandspa.com, from $139).
DRIVING TIP The quickest way to get to Excelsior Springs: Catch I-35 North from downtown Kansas City, then take Highway 69 to Excelsior.
Sleepy Hollow, N.Y.
30 miles from New York City
Indulge your love of literature, the arts, and lifestyles of the rich and famous in this storied region north of New York City.
Ichabod Crane and the Headless Horseman live on (in spirit, anyway) in the Sleep Hollow Cemetery, which author Washington Irving name-checked in his 1820 story "The Legend of Sleepy Hollow." Walk the grounds for free and visit cemetery residents including Irving himself, Andrew Carnegie, Elizabeth Arden, and William and J.D. Rockefeller, or take a two-hour, lantern-lit guided evening tour—if you dare (914/631-0081, sleepyhollowcemetery.org, guided tour $25). For a quick bite, select a hot "Fleetwood original" calzone (stuffed with pepperoni, sausage, peppers, onions, mozzarella, and tomato sauce) from Fleetwood Pizzeria, founded by the Guzzo family in 1965 (914/631-3267, fleetwoodpizza.com, $5.75). Drive two miles northwest, on Bedford Road, to Pocantico Hills to see how the other half lived at Kykuit: The Rockefeller Estate. Drift through the main rooms of the six-story stone house, past the fountains and sculptures dotting the expansive gardens, and tour the underground art galleries, replete with works by Picasso and Warhol (914/631-8200, hudsonvalley.org/historic-sites/kykuit/tours, from $23).
WHERE TO STAY Venture eight miles north of Sleepy Hollow to bunk at the Alexander Hamilton House, an eight-unit Victorian B&B with an eight-foot-deep swimming pool and a giant lawn chess set in the backyard (914/271-6737, alexanderhamiltonhouse.com, from $135).
DRIVING TIP Allow traveling time for New York City traffic—the 25-mile drive can take much longer than an hour, even during off-peak hours.