Long weekend trips are like a right of passage for most Americans. That extra day goes a very long way to opening the door to road trips that can be a tight squeeze into the standard weekend.
The long weekend trip itineraries below are the perfect excuse to hit the road and escape the daily grind. Whether you’re craving the energy of the city, the tranquility of nature, or the charm of small towns, a three-day road trip is the ticket.
Now, let’s discover some of the best long weekend getaways in every corner of the U.S.
Related22 U.S. Road trips to take before you die
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Olympic Peninsula Loop (Washington)
Start/End: Seattle
- Day 1: Start in Seattle and take a ferry across Puget Sound to Bainbridge Island. Then, drive to the historic town of Port Townsend to see spectacular Victorian architecture. Round out the day by heading to Olympic National Park.
- Day 2: Spend your day hiking in Olympic National Park. Start with a visit to Hurricane Ridge for incredible mountain views, then venture into the park’s diverse ecosystems, including temperate rainforests and alpine meadows.
- Day 3: Explore the Hoh Rainforest and walk the Hall of Mosses trail to see towering trees draped in lush green moss. Then, head to the coast to see the dramatic sea stacks at Rialto Beach before returning to Seattle.
Highlights: This long weekend trip features ferry rides with stunning views, explore Victorian towns, hike in diverse ecosystems, and visit a temperate rainforest.
Pacific Coast Highway (California)
As one of America’s most iconic roads, we couldn’t not mention this one. It’s a great route for long weekend trips starting anywhere from San Diego to Northern California.
RelatedPacific Coast Highway road trip guide
Start/End: San Francisco
- Day 1: Begin your journey in San Francisco by driving across the Golden Gate Bridge, then meander to Santa Cruz to stroll along the boardwalk and bunk up for the night.
- Day 2: Head to Monterey for the world-renowned Monterey Bay Aquarium and stroll through Carmel-by-the-Sea to close out your day.
- Day 3: Drive the stunning stretch of Highway 1 to Big Sur, stopping at Bixby Creek Bridge, then roll back to San Francisco.
Highlights: A long weekend trip with roller coaster rides on the Santa Cruz boardwalk, the underwater world at Monterey Bay Aquarium, and coastal trail hikes in Big Sur.
Canyonlands and Arches National Parks (Utah)
Start/End: Moab
- Day 1: Fire things up in Moab, a small town surrounded by some of the most spectacular landscapes in the American Southwest. Spend your first day exploring Arches National Park, known for its over 2,000 natural stone arches.
- Day 2: Head to Canyonlands National Park to explore the vast canyons and mesas of the Island in the Sky district. Take a hike to Mesa Arch for a stunning sunrise view, or drive the Shafer Trail for a thrilling off-road adventure. In the afternoon, visit Dead Horse Point State Park for panoramic views of the Colorado River winding through the canyon below.
- Day 3: Spend your final day exploring the lesser-known Needles district of Canyonlands National Park. Hike the Chesler Park Loop or the Joint Trail to see the park’s unique rock formations and colorful spires. End your trip with a scenic drive along the Colorado River before returning to Moab.
Highlights: Hike to iconic arches and mesas, explore off-road trails, and enjoy panoramic canyon views.
Black Hills and Badlands (South Dakota)
Start/End: Rapid City, SD
- Day 1: Begin your road trip in Rapid City, the gateway to the Black Hills. Spend your first day exploring Mount Rushmore National Memorial. Afterward, visit the nearby Crazy Horse Memorial, a massive mountain carving dedicated to the Lakota leader.
- Day 2: Explore the natural beauty of the Black Hills by visiting Custer State Park, home to a large herd of bison and scenic drives like the Needles Highway. Take a hike to Sylvan Lake or explore the park’s many other trails. Spend the night in the town of Deadwood, known for its Wild West history and historic Main Street.
- Day 3: On your final day, venture into Badlands National Park, known for its striking geological formations and rugged beauty. Drive the Badlands Loop Road to see the park’s dramatic landscapes.
Highlights: See iconic monuments, hike scenic trails, explore historic Wild West towns, and drop your jaw at spectacular geological formations.
Route 66 Mini-Adventure (Arizona)
Start/End: Flagstaff
- Day 1: Flagstaff is a mountain town brimming with historic charm that’s not too far from Phoenix. Take a short drive from Flagstaff to Williams, where you can hop on the Grand Canyon Railway for a scenic ride to the South Rim. The town’s retro diners and Route 66 memorabilia are a must-stop for a scoop of The Mother Road.
- Day 2: Continue your journey westward to Seligman, a quirky town that inspired Pixar’s Cars. Spend some time exploring the roadside attractions, like Delgadillo’s Snow Cap Drive-In, where you can enjoy an old-fashioned burger and shake.
- Day 3: Spend your last day in Kingman, where you can visit the Route 66 Museum to learn about the history of this iconic highway. Don’t miss a side trip to the ghost town of Chloride for a taste of the Wild West. As evening falls, take the short 2.5-hour drive back to Flagstaff.
Highlights: Ride a historic train to the Grand Canyon, explore quirky Route 66 towns, and visit a ghost town on this long weekend trip.
Route 66 from Chicago to Springfield (Illinois)
Start/End: Chicago
- Day 1: Start your Route 66 adventure in Chicago, the birthplace of the Mother Road. Explore the city’s iconic landmarks, such as Millennium Park and the Art Institute of Chicago. In the afternoon, begin your journey down Route 66, stopping in Joliet to visit the Route 66 Raceway and the Joliet Area Historical Museum.
- Day 2: Continue your journey to Pontiac, a town known for its vibrant murals and Route 66 memorabilia. Visit the Route 66 Hall of Fame and Museum and take a walk along the city’s mural tour, which features over 20 large-scale works of art. In the evening, you could zip to Bloomington for the night or bunk up in Pontiac.
- Day 3: Last stop = Springfield, the capital of Illinois and the home of Abraham Lincoln. Visit the Abraham Lincoln Presidential Library and Museum to learn about the life of the 16th president, and tour his historic home. Before heading back to Chicago, stop by the Cozy Dog Drive-In, a Route 66 icon known for its famous corn dogs.
RelatedThe Ultimate Route 66 Road Trip
Highlights: Explore iconic Route 66 landmarks, visit museums and historic homes, and learn about Abraham Lincoln’s life.
Texas Hill Country
Start/End: Austin
- Day 1: Start your road trip in Austin, the capital of weirdly cool things. After fueling up on breakfast tacos, head to Dripping Springs to tour a cool blend of distilleries and wineries. Cool off with a swim in the natural beauty of Hamilton Pool, a shimmering limestone grotto.
- Day 2: Roll to Luckenbach, known for its famous placement in a country song. Spend the day listening to live music under the oak trees before heading to Fredericksburg, where you can indulge in wine tasting at one of the many vineyards.
- Day 3: Spend your final day discovering Enchanted Rock State Natural Area. Hike to the summit for breathtaking views of the surrounding Hill Country, then reward yourself with a hearty German meal in Fredericksburg before circling back to Austin.
Highlights: Sip on local spirits in Dripping Springs, enjoy live country music in Luckenbach, hike to the top of Enchanted Rock, and enjoy authentic German cuisine.
Nashville to Great Smoky Mountains National Park (Tennessee)
Start/End: Nashville
- Day 1: Fire up your road trip in Nashville, the vibrant heart of country music. Start your day by visiting the Country Music Hall of Fame before heading to Broadway to experience the lively atmosphere of honky-tonk bars. The Johnny Cash Museum is another must-see on our list here.
- Day 2: Hit the road and drive east from Nashville towards Great Smoky Mountains National Park. On the way, stop in Gatlinburg, where you can unwind in a cozy mountain cabin or enjoy a relaxing evening strolling through the town’s quaint shops and restaurants.
- Day 3: Get started early to explore Great Smoky Mountains National Park. Begin with a scenic drive along Newfound Gap Road for epic vistas of the mountains and valleys. Afterward, explore some of the park’s picturesque trails, such as the Laurel Falls Trail or the Alum Cave Trail.
Before heading back to Nashville at night, enjoy a leisurely picnic by one of the park’s tranquil streams or waterfalls.
Highlights: Experience the vibrant music scene of Nashville, enjoy theme park thrills or historical attractions in Pigeon Forge, take in breathtaking mountain views, hike scenic trails, and relax in the beauty of the Smokies.
Florida Keys
Start/End: Miami
- Day 1: Start your long weekend getaway in Miami, then hit the Overseas Highway, one of America’s most scenic drives. Your first stop is Key Largo, where you can dive into the underwater wonders of John Pennekamp Coral Reef State Park.
- Day 2: Continue your island-hopping long weekend, stopping at Bahia Honda State Park, known for its sandy beaches and crystal-clear waters. Cross the famous Seven Mile Bridge and reach Key West in time for the sunset celebration at Mallory Square.
- Day 3: Spend your final day exploring Key West. Visit the Ernest Hemingway Home and Museum, where you can learn about the famous author and his six-toed cats, stroll down lively Duval Street, and take a ride on the Conch Tour Train to see the sights. The return drive to Miami is on the longer side for a long weekend trip, so be sure to leave Key West in time for the 3.5(ish) hour drive back.
Highlights: Snorkel in coral reefs, relax on pristine beaches, watch sunset celebrations, and tour historic homes on this long weekend trip.
Shenandoah Valley and Skyline Drive (Virginia)
Start/End: Washington, D.C.
- Day 1: Depart from Washington, D.C., and head to Shenandoah National Park, where you’ll spend the day driving along Skyline Drive. Stop at overlooks to take in the views and hike some of the park’s shorter trails, like the Stony Man Trail or the Limberlost Trail.
- Day 2: Continue your exploration of the Shenandoah Valley with a visit to Luray Caverns, the largest cavern in the eastern United States. Don’t miss the Great Stalacpipe Organ, which creates music by tapping the natural formations. In the afternoon, visit the nearby Shenandoah Vineyards for a wine tasting with a view.
- Day 3: Spend your final day exploring the charming town of Staunton, known for its well-preserved historic buildings and vibrant arts scene. Visit the Frontier Culture Museum to learn about the region’s history, or catch a performance at the American Shakespeare Center, home to the world’s only replica of Shakespeare’s Blackfriars Playhouse.
Highlights: Drive scenic mountain roads, explore underground caverns, taste local wines, and experience living history.
Catskills and Hudson Valley (New York)
Start/End: New York City
- Day 1: Escape the city and head north to the Hudson Valley, starting with a visit to the Storm King Art Center, an expansive outdoor sculpture park that blends art with nature. Continue to the historic town of New Paltz, where you can explore the centuries-old Huguenot Street and its stone houses.
- Day 2: Drive deeper into the Catskills and spend the day hiking in the Mohonk Preserve or Minnewaska State Park. Trails like the Labyrinth and Lemon Squeeze offer exciting rock scrambles with stunning views of the Shawangunk Ridge.
- Day 3: Explore the nearby Kaaterskill Falls, one of the highest waterfalls in New York, or take a scenic drive along the winding mountain roads. Before heading back to the city, stop by a local farm or winery in the Hudson Valley for a taste of fresh produce and artisanal goods.
Highlights: Explore outdoor art installations, hike challenging trails with rewarding views, visit historic sites, relax in artsy small towns as part of this long weekend trip.
The Berkshires (Massachusetts)
Start/End: Boston
- Day 1: Leave Boston behind and drive west to the Berkshires, a picturesque region known for its rolling hills and cultural attractions. Begin your trip in Stockbridge, home to the Norman Rockwell Museum, where you can see original works by the beloved American illustrator. In the afternoon, take a stroll through the quaint town center for more history and culture.
- Day 2: Spend the day exploring the outdoors by hiking the trails of Mount Greylock, the highest peak in Massachusetts. The views from the summit are stunning, especially during the fall when the foliage is at its peak. In the evening, catch a performance at Tanglewood, the summer home of the Boston Symphony Orchestra, or catch a show at a local theater.
- Day 3: On your final day, visit the Massachusetts Museum of Contemporary Art (Mass MoCA) in North Adams, one of the largest contemporary art museums in the U.S. Before heading back to Boston, stop by the town of Lenox for to check out the shops and restaurants in its hip downtown area.
Highlights: Explore art museums, hike scenic mountain trails, enjoy live music and theater performances.
Tips for Making the Most of a Long Weekend Getaway
- Plan Ahead, But Stay Flexible: Have a general itinerary set, but be open to spontaneous detours and discoveries along the way. Sometimes the best experiences come from unplanned stops.
- Start Early: Make the most of your days by hitting the road early. This allows you to avoid traffic, enjoy more daylight, and see more sights.
- Take Breaks: Don’t forget to stretch your legs and take breaks during your drive. This helps prevent fatigue and gives you a chance to explore unexpected roadside attractions.
- Stay Connected, But Disconnect When Needed: While it’s important to stay in touch with loved ones and use GPS for navigation, also take time to unplug and enjoy the scenery. Take photos, but don’t forget to live in the moment.
- Book Accommodations in Advance: Especially during peak travel seasons, booking your accommodations ahead of time ensures you have a comfortable place to stay each night without the stress of last-minute searching.
- Be Prepared for Anything: Whether it’s a sudden change in weather or an unexpected detour, be ready to adapt to whatever the road throws your way. Keep a positive attitude and embrace the adventure.
- Capture the Memories: Take lots of photos, jot down your thoughts in a travel journal, and/or talk about your experiences with loved ones at the close of each travel day.
RelatedAmerica’s weirdest, wildest, and raddest roadside attractions
A long weekend road trip is the perfect way to break away from routine and dive into new adventures. Whether you’re cruising down the iconic Route 66, soaking in the natural wonders of the Great Smoky Mountains, or exploring the vibrant cultures of American cities, these long weekend itineraries offer a perfect blend of adventure, relaxation, and discovery.
And remember, our Autopilot™ app is here to help you customize your very own long weekend trip from any U.S. starting point you choose. Happy trails!
