9 Ultimate Weekend Road Trips You Can Take from Major US Cities

Beyond the capital lie the scenic Blue Ridge Mountains filled with pine and oak trees and bathed in a dark blue hue. Make your base the Graduate Charlottesville, a handsome boutique hotel in a town cloaked in Colonial charm and known for its former presidential residents, James Monroe and Thomas Jefferson. Although Jefferson’s Monticello estate tops many a sightseeing list, set time aside to stroll the Historic Downtown Mall, a brick pedestrian hub in the heart of C-ville that’s a foodie paradise: there’s the Spanish small plates at Mas Tapas, Southern soul food at Ace Biscuit & Barbecue, and upscale French cuisine at Fleurie Restaurant. Some of Virginia’s best vintages are produced at the area’s more than 20 wineries. Among those worth a visit: Barboursville, Pippin Hill, and White Hall. Prefer hops? Don’t miss South Street Brewery on the Brew Ridge Trail.

Just off California’s Highway 1 is the quaint Carmel-by-the-Sea, a strip of windswept coastline popular for its dramatic beaches and thriving arts scene. Check into La Playa Carmel hotel before heading to San Carlos and Dolores streets to tour eye-popping galleries like James J. Rieser Fine Art, Gallerie Amsterdam, and Classic Art Gallery. A 20-minute drive southeast, you’ll find Carmel Valley, where stylish boutiques and bistros line the streets. Sip flights of wine at the Georis Winery, then continue the wine crawl at L’Auberge Carmel’s intimate restaurant, which, despite its small size, hides a 4,500-bottle-strong cellar downstairs.

Not far from the brazen bodies of the hot Miami scene is this quiet four-mile island that's packed with history and a surprising number of top-notch restaurants. Stay at Casa Marina Resort, and start the morning off with a café con leche at White Street Sandwich Shop. A five block walk leads to El Siboney Restaurant, an authentic Cuban spot in a low-key residential hood where you can tuck into a heaping plate of black beans, plantains, roast pork, and yellow rice. Afterwards, get a feel for Key West’s literary history with a visit to Ernest Hemingway Home and Museum, then head to Duval Street for some boutique-hopping: Wanderlust and Lippy's Hot Hats are two favorites.

If you picture the Rockies as a winter-only escape, think again. Come summer, Breckenridge morphs into a playground for adrenaline junkies. Ride Peak 8 Fun Park’s luge-style SuperSlide or hop on the new two-stage zipline. The Adventure Company offers full moon white-water rafting trips, complete with glow sticks and a fajita feast at the end of the white-knuckling trip. Looking for more relaxed pursuits? There’s free, weekly outdoor concerts in the Arts District, culminating with the 10-day Breckenridge International Festival of Arts in August. Or, you could spend your days sampling local brews. Start at Canteen Tap House and Tavern, followed by Après Handcrafted Libations, or Warming Hut. It's also worth checking out Broken Compass and Breckenridge breweries. Don’t worry—the Free Ride bus can take you home if you’ve had one (or two or three...) too many.

This classic waterfront town has all the trappings of a quintessential New England escape, from the sleepy harbor and sandy beaches to fresh lobster and postcard-perfect views. Settle in at Nonantum Resort, which dates back to 1884, before exploring Dock Square’s charming boutiques. We love Coastal Jewelers for its Tourmaline gems mined in Maine and Sea Glass Jewelry Studio, which sells pendants in vibrant emerald green, milky white, and hazy aqua hues. Hop on a cruiser from Kennebunkport Bicycle, and make your way to Goose Rocks Beach, an ideal place to kick-back with a summer read. For dinner, there's the upscale Earth at Hidden Pond. What to order? The wood-fired lobster pot pie for two with minted peas and potatoes has become a cult favorite.

Despite its rainy reputation, Bend is coveted by Portlanders as one of the West Coast’s best-kept secrets due to its glorious summers and craggy terrain. The Old Mill District, a historic area comprised of shops, restaurants, and galleries, is intersected by a calm strip of the 252-mile Deschutes River, where families paddle-board and tube under pedestrian bridges. Summer jams play from the riverfront Les Schwab Amphitheater, which hosts headliners like Alabama Shakes. Nosh on West Coast sushi and innovative Thai plates at 5 Fusion & Sushi Bar, helmed by James Beard-nominated chef Joe Kim. We recommend the shogun roll with unagi, escolar, spicy salmon, tempura, and avocado. Do like the locals do and hit the trails: Smith Rock is a hardcore climber’s heaven thanks to its challenging spires, while South Canyon Reach is ideal for novice hikers. Just don't forget your camera.