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


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This article was originally published on Jetsetter.com. Both Jetsetter and Viator are part of the Tripadvisor Media Group. Follow Viator on Instagram at @viatortravel, and Tripadvisor at @tripadvisor.

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By Chelsea Stuart, Jetsetter.com

You've got the perfect playlist, a kick-ass new pair of shades, and the wide open road to explore. Now for the escape plan. Here are our favorite getaways within driving distance of top American cities, from LA to New York City. As if you needed another reason to look forward to Friday.


1. Ojai, California

Orange farms abound in Ojai, the capital of the sweet Ojai Pixie tangerines. Photo: Brandon DesJarlais / Unsplash

83 miles from LA

A quick 90-minute jaunt from LA, this Californian Shangri-La has all the essentials: palm tree-dotted landscapes, Spanish Revival architecture and a laid-back local culture. Recharge with a mud cleanse or an outdoor yoga class at the Mission-style Ojai Valley Inn & Spa, which overlooks the rolling green Topatopa Mountains. For lunch, try the garden fresh plates at Suzanne’s Cuisine or the Mexican-inspired dishes at Farmer and the Cook, where the organic ingredients are grown at the owners’ 16-acre farm. The Ojai Farmers’ Market (open Sundays) is the place to score regional gourmet goodies—get yours to go and have a picnic while watching the sunset from Meditation Mount.

2. Montauk, New York

Montauk Point Lighthouse sits at the easternmost point of Long Island. Photo: Laura Peruchi / Unsplash

117 miles from New York City

With fewer crowds and a low-key boho-chic vibe, the relaxed surfer haven of Montauk is the antithesis of see-and-be-seen Hamptons—the perfect East Coast road trip for anyone based in the big city. Shack up at Solé East Resort, which has a chill garden of fire pits, hammocks, and Adirondack chairs as well as outdoor yoga and live acoustic music on Sundays. If you didn't bring your own wheels, rent one of the hotel's ZipCars and grab an Aloha smoothie (fresh pineapple, coconut, mango and banana) to go from Joni's Kitchen before driving to Ditch Plains to hang ten with the surfer dudes and visit Montauk Point Lighthouse for a killer Instagram shot. Eat dinner al fresco at The Crow's Nest—we love the Montauk Dayboat scallops and local sea bass—or nosh on mouthwatering sushi (the crunch calamari roll with avocado and spicy tuna is a must) at Inlet Seafood Restaurant, the best spot to watch the sun set over the water. Later in the evening, head across the pond (to the other side of Fort Pond, that is) to check out the The Surf Lodge's preppy party scene.

3. Charlottesville, Virginia

Charlottesville is a gateway to Shenandoah National Park, which runs along a section of the Blue Ridge Mountains. Photo: Bruce Wilson / Unsplash

116 miles from Washington DC

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.

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4. Carmel-by-the-Sea, California

Visitors wander past galleries and shops in Carmel-by-the-Sea, California. Photo: Brittany Hosea-Small

123 miles from San Francisco

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.

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5. Grand Haven, Michigan

The piers of Lake Michigan are popular spots to catch sunrises and sunsets. Photo: Justin Heap / Unsplash

171 miles from Chicago

When you live in a landlocked state, a coastal vacation is not exactly on your drive-distance radar. Lucky for Chicagoans, Grand Haven's stretch of sugary sand is a damn good substitute. Most days are spent swimming in Lake Michigan's turquoise water, but if you want a break from the beach, the charming town has plenty to offer. Follow the locals to the divey Morning Star Cafe and make sure to order the Hawaiian ham crepe (thinly sliced ham, onion, cilantro, and habanero cheese topped with homemade pineapple salsa and honey mustard hollandaise) with a side of chorizo hash browns. For lunch, suck down plates of fresh oysters at The Grand Seafood & Oyster Bar, then walk three blocks to Snug Harbor and refresh with a martini on the rooftop deck. In the evening, there's no better place to catch the sunset than on the pier attached to the picture-perfect Grand Haven State Park Lighthouse.

6. Key West, Florida

Often visited on Historic District tours, tin-roofed conch houses are to Key West what mid-century architecture is to Palm Springs. Photo: Joshua Case / Unsplash

160 miles from Miami

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.

Find things to do in Key West

7. Breckenridge, Colorado

Mountain views and hiking trails abound in the year-round adventure destination of Breckenridge. Photo: Tevin Trinh / Unsplash

80 miles from Denver

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.

Find things to do in Breckenridge

8. Kennebunkport, Maine

Sandy beaches, restaurants serving fresh lobster, and sailboats moored off photoworthy docks—Kennebunkport offers up those quintessential Maine details. Photo: René Porter / Unsplash

84 miles from Boston

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.

Find things to do in Kennebunkport

9. Bend, Oregon

Smith Rock State Park, located less than 30 miles from Bend, draws outdoorsy travelers with its scenic views and hiking and climbing opportunities. Photo: Clint McKoy / Unsplash

163 miles from Portland

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.

Find out how to spend a day in Bend

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Hi, I'm Jetsetter!

This article was originally published on Jetsetter.com. Both Jetsetter and Viator are part of the Tripadvisor Media Group. Follow Viator on Instagram at @viatortravel, and Tripadvisor at @tripadvisor.

Keep exploring
See all USA tours
19,035 tours & tickets
See all things to do in USA
Gloria Casarez mural in Philly's Gayborhood
8 Tours That Celebrate Women’s History in the US