9 Amazing Weekend Road Trips You Can Take From Major US Cities – USA Trip Ideas

1. Road trip from Los Angeles to Ojai, CA: 83 miles (133 kilometers)

Bird's eye view of Ojai, the capital of the sweet Ojai Pixie tangerines.

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

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

Ojai is just a quick, 90-minute 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, NY: 117 miles (188 kilometers)

A landscape with the Montauk Point Lighthouse in Montauk, 117 miles from New York City.

Montauk Point Lighthouse sits at the easternmost point of Long Island. | Photo Credit: 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 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, VA: 116 miles (187 kilometers)

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. | Photo Credit: Bruce Wilson / Unsplash

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

Just a short drive 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.

Find things to do in Charlottesville

4. Road trip from San Francisco to Carmel, CA: 123 miles (198 kilometers)

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

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

Another worthwhile weekend road trip destination in California, but this time near San Francisco, is 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.

Find things to do in and around Carmel

5. Road trip from Chicago to Grand Haven, MI: 171 miles (275 kilometers)

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. | Photo Credit: 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 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, FL: 160 miles (257 kilometers)

Exterior of a tin-roofed conch houses at the Historic District in Key West.

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

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

A little under three hours 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.

Find things to do in Key West

7. Road trip from Denver to Breckenridge, CO: 80 miles (129 kilometers)

The mountains of Breckenridge, known to be a playground for adrenaline junkies.

Mountain views and hiking trails abound in the year-round adventure destination of Breckenridge. | Photo Credit: 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 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.

Find things to do in Breckenridge

8. Road trip from Boston to Kennebunkport, ME: 84 miles (135 kilometers)

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

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

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 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.

Find things to do in Kennebunkport

9. Road trip from Portland to Bend, OR: 163 miles (262 kilometers)

Golden hour at Smith Rock State Park in Bend.

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

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

Despite its rainy reputation, Bend 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.

A portion of this article was originally published via Jetsetter, a part of the Tripadvisor Media Group in 2020 and was recently updated by Justin Hartung.

Find out how to spend a day in Bend