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9 Amazing Weekend Road Trips You Can Take From Major US Cities

The best road trips (including the best things to do) near America’s biggest cities.

Hi, I'm Justin!

A writer and editor based in the Bay Area, Justin has worked in book, magazine, and digital publishing for more than two decades. When he's not dreaming about his next trip, he's planning a future restaurant adventure. He's written for New York Magazine, The Village Voice, Newsday, Google Play, Zagat Survey, and more.

You've got the perfect playlist, a stylish new pair of shades, a gassed-up ride, and no weekend plans … yet. Now for the perfect road trip destination. From relaxing coastal paradises to forested mountain hubs for adventures, we’ve mapped out the best weekend getaways within driving distance of top US cities (with a hefty emphasis on the most scenic way to get there). As if you needed another reason to look forward to Friday.

1. Road trip from Los Angeles to Ojai, California

Bird's eye view of Ojai, looking down at the orange and tangerine fields.
Ojai is the capital of the sweet Ojai Pixie tangerines.Foto: Brandon DesJarlais / Unsplash

A SoCal weekend getaway for relaxation and farm-fresh cuisine.

Ojai is just a quick, 83-mile (133 kilometers) drive from LA, and has all the essentials for a romantic weekend road trip: famous pink sunsets, impressive Spanish Revival architecture, and a laid-back local art scene. Take a pottery workshop, and recharge with a mud cleanse at the Mission-style Ojai Valley Inn & Spa, which overlooks the Topatopa Mountains.

For an unforgettable meal, try the wood-fired Californian cuisine at Rory’s or the Mexican-inspired dishes at Farmer and the Cook, where the ingredients are grown on the owners’ 16-acre farm. Fro those looking for more adventure, there’s also rock climbing, horseback riding, and guided hikes to explore the surrounding mountains.

2. Road trip from NYC to Montauk, New York

A landscape with the Montauk Point Lighthouse in Montauk.
Montauk Point Lighthouse is loated on the easternmost point of Long Island.Foto: Laura Peruchi / Unsplash

Super-fresh seafood and a low-key surfer vibe at the end of Lond Island.

With a quiet luxury appeal, the relaxed surfer haven of Montauk is 117 miles (188 kilometers) from New York City, and is the antithesis of the see-and-be-seen Hamptons. For the ultimate weekend road trip itinerary, leave New York City and shack up at Solé East Resort, which has a chill garden with fire pits and hammocks. Head to Ditch Plains to hang ten with the surfers and stop by Montauk Point Lighthouse, the oldest lighthouse in New York and the easternmost point on Long Island, for the best views. Enjoy a luxury beach bonfire and picnic dinner on the beach, or charter a fishing boat and catch your own dinner for the night.

3. Road trip from DC to Charlottesville, Virginia

The Blue Ride Mountains as seen from the Shenandoah National Park in Charlottesville.
Charlottesville is a gateway to Shenandoah National Park, which runs along a section of the Blue Ridge Mountains.Foto: Bruce Wilson / Unsplash

On this fun weekend road trip, you'll find colonial charm, wine, and a stellar dining destination.

Just 116 miles (187 kilometers) from the capital, you’ll be dazzled by the Blue Ridge Mountains as your scenic backdrop. Make your base the Graduate Charlottesville, a handsome boutique hotel, then explore highlights like Thomas Jefferson’s Monticello estate, a UNESCO World Heritage Site, and the Historic Downtown Mall, a charming pedestrian hub and foodie paradise: Try Spanish small plates at Mas Tapas; Southern soul food at Ace Biscuit & Barbecue; or upscale French cuisine at Fleurie Restaurant. And be sure to check out some of the best things to do in Charlottesville, including the wineries, such as Barboursville, Pippin Hill, and White Hall.

4. Road trip from San Francisco to Carmel, California

Street view of one of the commercial streets in Carmel-by-the-Sea in California.
Charming galleries and shops abound in Carmel-by-the-Sea, California.Foto: Brittany Hosea-Small / Tripadvisor

Take a romantic road trip away from the bustle of the Bay Area.

Another worthwhile weekend road trip destination in California, this time just 123 miles (198 kilometers) from San Francisco along California’s Highway 1. Here you’ll find the quaint and charming Carmel-by-the-Sea, a town on a windswept coastline famous for its dramatic beaches, fairytale cottages, 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. Sip flights of wine at a nearby winery, or head out on a boat for a whale-watching adventure off the California coast. If you want to make your adventure a true road trip, keep driving south and book a tour of Hearst Castle, an absolute must-do for any California road trip.

5. Road trip from Chicago to Grand Haven, Michigan

Visitors view the sunset at a pier in Lake Michigan in Grand Haven.
The piers of Lake Michigan are popular spots to catch sunrises and sunsets.Foto: Justin Heap / Unsplash

Indulge in relaxing beach vibes at this charming lakeside getaway on Lake Michigan.

For Chicagoans, Grand Haven's stretch of sugary sand is just 171 miles (275 kilometers) from the Windy City, and makes a terrific destination for a family-friendly weekend road trip. Most days can be spent swimming in Lake Michigan's turquoise water, but the charming lakeside town also has plenty to offer. Head to local favorite Morning Star Cafe for a Hawaiian ham crepe, or suck down plates of fresh oysters at The Grand Seafood & Oyster Bar. Then walk three blocks to Snug Harbor and refresh with a drink and snack 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. Road trip from Miami to Key West, Florida

Exterior of a tin-roofed conch houses at the Historic District in Key West.
Tin-roofed conch houses are to Key West what mid-century architecture is to Palm Springs.Foto: Joshua Case / Unsplash

History, coffee, and Cuban food reign in this southernmost US city.

An easy and smooth 160 miles (257 kilometers) from Miami is a (mostly) quiet 4-mile (6-kilometer) Key West is packed with history and a surprising number of top-notch restaurants. Stay at Casa Marina Resort, and start the morning with a café con leche at Keys Coffee Co. A 5-block walk leads to El Siboney Restaurant, where you can tuck into a heaping plate of authentic Cuban food. Afterward, 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. Also, located at the end of Duval Street is the Southernmost Point of the Continental USA monument, a free, fun photo op.

7. Road trip from Denver to Breckenridge, Colorado

The mountains of Breckenridge are known to be a playground for adrenaline junkies.
Mountain views and hiking trails abound in the year-round adventure destination of Breckenridge.Foto: Tevin Trinh / Unsplash

Explore mountain thrills and a booming beer scene with this adventure weekend road trip.

If you picture the Rockies as a winter-only escape, think again. Come summer, the historic mining town of Breckenridge, 80 miles (129 kilometers) from Denver, morphs into a playground for adrenaline junkies. Catch some thrills by riding Peak 8 Base Camp’s luge-style SuperSlide and two-stage zipline, or try whitewater rafting trips. Looking for more relaxed pursuits? Enjoy free, weekly outdoor concerts in the Arts District or the Breckenridge International Festival of Arts in August. Brew-heads should check out The Canteen, Après Handcrafted Libations, and Broken Compass. Don’t worry—there’s a free shuttle to take you home if you’ve had a few too many.

8. Road trip from Boston to Kennebunkport, Maine

Sailboats moored off photoworthy docks in Kennebunkport, Maine.
Sandy beaches and fresh lobster—Kennebunkport offers up quintessential Maine experiences.Foto: René Porter / Unsplash

A coastal gem in Maine with a scenic weekend drive that is half the fun.

This classic waterfront town, 84 miles (135 kilometers) from Boston, 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 and Sea Glass Jewelry Studio, which sells pendants in vibrant emerald green, milky white, and hazy aqua hues. Join a guided Kennebunkport tour to learn about 200 years of history, and visit Goose Rocks Beach, an ideal place to kick back with a summer read. For a scenic, upscale dinner in a natural setting, try Earth at Hidden Pond.

Related:Epic Fall Foliage Road Trips To Drive This Year.

9. Road trip from Portland to Bend, Oregon

Golden hour at Smith Rock State Park in Bend.
Smith Rock State Park draws outdoorsy travelers with its scenic views and hiking and climbing opportunities.Foto: Clint McKoy / Unsplash

A hidden gem in the Pacific Northwest, Bend is a hiker’s paradise.

Despite its rainy reputation, Bend, located 163 miles (262 kilometers) from Portland, is one of the West Coast’s best-kept secrets due to its glorious summers and glorious hiking. The Old Mill District, a historic area with shops, restaurants, and galleries, is intersected by the Deschutes River, where families paddle-board and tube. Nosh on sushi and innovative Thai plates at Five Fusion & Sushi Bar, then check out a riverside concert at the Les Schwab Amphitheater. Or, to keep your weekend road trip affordable, hit one of the many hiking trails: Smith Rock is a hardcore climber’s heaven, thanks to its challenging spires, while South Canyon Reach is ideal for novice hikers.

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