Summary of Long Weekend Getaways
When planning a trip for a long weekend, there’s a lot to consider—choosing a destination far enough to feel like a getaway yet close enough not to spend the weekend in transit is crucial. You want a place rich in activities without overwhelming options. With Memorial Day fast approaching, we have compiled top destinations for long weekend getaways this year, integrating editorial insight and relevant data.
Craving a nature escape? Spend a day or two exploring Mt. Hood National Forest near Portland, where hiking, skiing, and breathtaking views await. If art draws you in, head to Hudson, New York, just two hours from NYC, to discover art galleries, vintage shops, and unique boutiques. These destinations, along with our top picks, provide a convenient travel experience filled with various activities perfect for a 72-hour itinerary.
Utilize this list to design your ideal long weekend getaways this year, whether for Memorial Day, Labor Day, or any time you can add an extra day to your usual weekend.
01 of 12 – Key West, Florida
Address: Key West, FL 33040, USA
When in Florida, consider visiting the Southernmost Point instead of venturing outside the state. From Miami, it’s about a three-hour drive. Stay at the Perry Hotel in Stock Island—a serene, dog-friendly retreat away from the downtown crowds, yet close to famed Duval Street. Explore the Hemingway Home and enjoy drinks at the Green Parrot Bar, a destination favored by Hemingway since the 1800s. Don’t miss Mallory Square’s Sunset Celebration with fire-breathers, psychics, and street performers. Nearby, indulge in a meal and a mojito at El Meson de Pepe, featuring the island’s only live Cuban band. Set time aside for watersports—boating, jet-skiing, swimming, and snorkeling unveil the wonders below the surface of the sea.
02 of 12 – Mt. Hood, Oregon
Address: Mt Hood, Oregon 97041, USA
While in Portland, don’t merely admire Mt. Hood—engage with it directly! Famous for its long ski season, Mt. Hood also offers numerous hiking trails, pristine alpine lakes, and stunning Cascade views. Stay at The Timberline Lodge, a beautifully preserved landmark from 1936 with cozy charm. Guests can enjoy dining at Timberline’s eateries or sip local brews at Mt. Hood Brewing Company in Government Camp. Take the scenic route, driving alongside the majestic Columbia River Gorge, with stops at Multnomah Falls—Oregon’s tallest waterfall—before heading up the mountain.
03 of 12 – Tupelo, Mississippi
Address: Tupelo, MS, USA
Known as the birthplace of Elvis Presley, any visit to this charming Mississippi town should include a stop at Elvis’s beginnings. Explore downtown, featuring Tupelo Hardware Company, where Elvis acquired his first guitar, and relive history at Johnnie’s Drive-In, famous for the burgers Elvis loved. Beyond Elvis, Tupelo is set in beautiful hills and provides easy access to the historic Natchez Trace Parkway. Don’t miss getting Connie’s Fried Chicken’s delicious blueberry doughnuts, or enjoy rural Secluded experiences at Moon Lake Farm B&B, which offers fishing and horseback riding.
04 of 12 – San Marcos, Texas
Address: San Marcos, TX, USA
San Marcos, home to Texas State University and popular outlet malls, offers more than just shopping. The spring-fed San Marcos River flows through downtown, perfect for inner tubing. Nature enthusiasts should explore Purgatory Creek Natural Area, with nine miles of trails winding through meadows and bluffs. Refuel at Industry, a trendy café, or quench your thirst at AquaBrew Brewery & Beer Garden. For the night, the Crystal River Inn presents an upscale yet intimate B&B experience.
05 of 12 – Ojai, California
Address: Ojai, CA 93023, USA
Only two hours from Los Angeles, Ojai offers an escape from urban life. With its majestic oaks, expansive citrus groves, and stunning Topatopa Mountains, it’s perfect for hikers and bikers. Consider a Cloud Climber Jeep tour for an adventure. This town hosts farmers alongside artists and makers, leading to unique shops and delightful local cuisine. Notably, it features the world’s largest open-air bookstore, Bart’s, alongside many dining establishments that source locally produced goods. Accommodation ranges from glamorous Airstreams at Caravan Outpost to luxurious experiences at historic establishments.
06 of 12 – Prince Edward County, Ontario, Canada
Address: Prince Edward, ON, Canada
Prince Edward County is ideal for a relaxing lake weekend. Positioned on Lake Ontario’s northeastern shore, the area boasts numerous sandy beaches like Sandbanks Provincial Park, home to the largest baymouth barrier dune formation in the world. Family-friendly Outlet Beach features shallow waters, while Dunes Beach’s pale sands offer breathtaking views. Local markets provide culinary delights, alongside more than 40 wineries and breweries perfect for keeping your thirst quenched.
07 of 12 – Athens, Georgia
Address: Athens, GA, USA
Athens, known for the University of Georgia, is just one hour from Atlanta and a top spot for food and music lovers. Stay at the historic Graduate Hotel downtown, and kick off your journey with local beers at Creature Comforts and Terrapin breweries. Enjoy seasonal Southern cuisine at Hugh Acheson’s acclaimed Five and Ten, and conclude your evening with live music venues like 40 Watt and Georgia Theatre, where legendary bands started their journeys.
08 of 12 – Boulder, Colorado
Address: Boulder, CO, USA
Boulder is an easy day trip from Denver, showcasing the best of Colorado with over 20 breweries, including the award-winning Avery Brewery. Hiking trails through the scenic Chautauqua Park at the Flatirons, rock climbing at Boulder Canyon, and water sports at Boulder Reservoir are just some of the outdoor activities available. In the evenings, stroll through downtown’s Pearl Street, lined with lively bars and restaurants.
09 of 12 – Valle de Bravo, Mexico
Address: Valle de Bravo, State of Mexico, Mexico
A two-hour drive from Mexico City leads you to picturesque Valle de Bravo. Its main square, colonial church, and lake encourage various water sports, such as sailing and paddleboarding. Surrounded by wooded mountains, outdoor enthusiasts will find abundant hiking and biking trails. For relaxation, wander the cobblestoned streets or shop for artisanal crafts. A delightful dining experience can be found at Los Pericos, a floating restaurant with excellent seafood and stunning views. Cap off your day at Hotel Rodavento, known for its tranquil spa treatments and premium accommodations.
10 of 12 – Hudson, New York
Address: Hudson, NY 12534, USA
Located on the east side of the Hudson River, Hudson is a creative sanctuary for artists, chefs, and nature aficionados, just over two hours from New York City. The Wick, a boutique hotel, housed in a former candle factory, showcases artistic designs, while Backbar offers a vibrant atmosphere within antiques. When exploring, take time to hike or bike within the surrounding scenic mountains.
11 of 12 – Indianapolis
Address: Indianapolis, IN, USA
While historically recognized as a sports town, Indianapolis has been evolving into a culinary and cultural hotspot. Popular neighborhoods include White River State Park, Fountain Square, Broad Ripple Village, and Mass Avenue. At Newfields, a sprawling 52-acre complex housing the Indianapolis Museum of Art, enjoy its lush gardens. Families will cherish a visit to the Children’s Museum of Indianapolis, the largest in the world. Stay in downtown accommodations like The Alexander, featuring contemporary design, and indulge your taste buds at Bluebeard, celebrated for unique cocktails and connections to local farmers.
12 of 12 – Madeline Island, Wisconsin
Address: Madeline Island, Wisconsin, USA
Madeline Island, the largest of the Apostle Islands, is renowned for its rocky sea caves. Start your day with a gourmet breakfast at Bayfield’s Old Rittenhouse Inn, followed by a ferry ride to explore this hidden gem in the Midwest. Kayak through the sea caves, rent bicycles, or take a cruise around the neighboring islands where you can learn about the Apostle Islands and their significance in Native American culture. Afterwards, unwind with a drink at Tom’s Burned Down Cafe, featuring live music and a quirky atmosphere.
