Springtime is one of the best times to explore top destinations across the USA. May offers mild weather, blooming flowers, and a colorful bouquet of unique events and activities. Whether you're seeking trending vacation destinations, some quick family-friendly fun, a solo adventure opportunity, or thrills in the Great Outdoors, you’ll find there's a wealth of spring adventures fit for your distinctive style. Here’s our pick of the best places to travel in May.
Trending Destinations
From the colorful tulip fields of Holland, Michigan, to the historic charm of Annapolis, Maryland, and beyond, these trending May vacation destinations offer a mix of colorful cultural festivals, thrilling outdoor activities, and unique local attractions. Whether you're a history buff, a music lover, or just looking for an escape from cloudy cool-weather blues, consider these trending trips for your next mid-spring adventure.
Holland, Michigan
The picturesque town of Holland dazzles in May with the vibrant Tulip Time Festival. This celebration of Dutch heritage features millions of tulips in bloom, traditional dance performances, striking flower-themed parades, and plenty of authentic cuisine. Beyond the festival, you can explore beautiful outdoor attractions like Holland State Park—with quiet sandy beaches and stunning views of Lake Michigan. Don't miss the iconic Big Red Lighthouse and the scenic dune trails at Mt. Pisgah. For a taste of local produce and artisan treats, visit the Holland Farmers Market, which opens in mid-May.
Annapolis, Maryland
Annapolis has a rich maritime history—and in May, the Wednesday Night Sailboat Races offer a thrilling spectacle where you can watch sailboats race across Chesapeake Bay. Visit the United States Naval Academy for guided tours and a fascinating look into the life of midshipmen. Or take a deeper dive into the city’s seafaring past at the Annapolis Maritime Museum, which features engaging exhibits, educational programs for all ages, and stunning waterfront views. The city in spring is also adorned with beautiful May Day flower displays, making it a perfect time for a stroll through the historic downtown.
Louisville, Kentucky
Louisville is synonymous with many things: bourbon, baseball bats, and—most of all—the Kentucky Derby. Held on the first Saturday in May, this historic horse race is an exciting, must-see event replete with extravagant hats, mint juleps, and lots of energy. Take a tour of the Bourbon Trail to sample some of the finest in the world. And don’t forget to bring the whole family to the Louisville Slugger Museum & Factory for a fascinating look into the history of baseball and the iconic bat. The city in spring also plays host to outdoor concerts and festivals at lovely Waterfront Park.
Memphis, Tennessee
May in Memphis means music at the Beale Street Music Festival, featuring top artists for a weekend of live performances. The mid-month World Championship Barbecue Cooking Contest at Liberty Park is a foodie’s dream in midtown, offering a sampling of mouthwatering barbecue from the best pitmasters in the country. Join in the fun of the Great American River Run for a foot race along the Mississippi River, while the Memphis in May International Festival celebrates the city's culture with family-friendly events, performances, and exhibitions. And since you’re here, be sure to squeeze in a visit to iconic Graceland and the National Civil Rights Museum.
New Orleans, Louisiana
The New Orleans Jazz & Heritage Festival is a May highlight, with performances by renowned jazz musicians and local artists. Walk the historic French Quarter to discover charming architecture, lively street performers, and delicious Creole cuisine. Additionally, the Garden District features beautiful historic homes and lush gardens—perfect for a leisurely stroll. One of the best ways to experience New Orleans is on a tour. Head to the bayous for a swamp tour (there’s plenty to choose from) to see the local wildlife and learn about the region's unique ecosystem. Or for a bit of spooky fun, join a Haunted History ghost tour.
Family-Friendly Fun
Because May offers milder weather, blooming flowers, and a vibrant array of events and adventures, it’s the perfect opportunity to make some travel memories. The mid-spring shoulder season typically means fewer crowds and lower prices—perfect for a quick family vacation that won’t break the bank. Whether you're looking to explore nature, learn something new, or simply enjoy quality time together, these family-friendly spots are sure to delight.
Austin, Texas
May in Austin is fantastic for family-friendly fun, and it all kicks off with the Pecan Street Festival, featuring local artisans, crafts, and hands-on workshops for kids. While in town, explore the Thinkery’s interactive exhibits indoors and discover educational outdoor activities kids will love at the Austin Nature & Science Center. For some more outdoor quality time, the Zilker Eagle Mini Train provides a scenic, relaxing ride through Zilker Park. In the evenings, head to the Congress Bridge and gaze in wonder at the spectacular flight of the bats, a uniquely-Austin experience. And, later in May, the whole family can chow down on unique eats at the Hot Luck food truck festival.
Orlando, Florida
Planning your Orlando vacation in May gives you access to the city’s top attractions without the stress of crowds. Of course, no trip to this part of Florida is complete without visiting theme parks like Walt Disney World and Universal Studios (and their new Universal Epic Worlds park, featuring five immersive worlds). But while you’re here, why not join in some family-friendly festival fun? The Epcot International Flower & Garden Festival showcases beautiful gardens, topiaries, and outdoor kitchens, while the SeaWorld Orlando Seven Seas Food Festival features over 180 culinary options and live performances. Enjoy interactive exhibits and educational programs for kids of all ages at the Orlando Science Center. Or take the aspiring astronaut in your family to Kennedy Space Center.
Solo Adventure Spots
Traveling solo can be an incredibly rewarding experience, offering the freedom to explore at your own pace and immerse yourself in new surroundings without distraction. So, take a trip with yourself this May! These cities are perfect for that kind of adventure, especially when the mid-spring weather is mild, the crowds are sparse, and there’s always something to do.
Charleston, South Carolina
With its charming, cobbled streets, historic buildings, and friendly locals, you'll find Charleston a welcoming spot for a solo trip. Start your adventure at Joe Riley Waterfront Park and relax by the iconic Pineapple Fountain for some people-watching. Then, take a stroll down Rainbow Row to see the colorful Georgian-style row homes and soak in the beauty of Charleston Harbor. May is festival season in Charleston, so don't miss the Spoleto Festival, a celebration of performing arts that transforms the city into a cultural hub; while the Piccolo Spoleto Festival offers a more intimate experience with local artists and performances.
For a great solo dining experience, check out Edmund's Oast Restaurant for a fine casual craft brew-pub experience with a seasonally-focused kitchen. When the sun sets, Charleston's nightlife often heads to the rooftops. Visit The Rooftop at the Vendue for sweeping views and delightfully inspired cocktails. For a more laid-back atmosphere, Revelry Brewing & Rooftop offers the perfect vibe.
Palm Springs, California
Start your Palm Springs solo adventure in the historic downtown area, where you can shop the day away through dozens of unique boutiques and galleries. For nature enthusiasts, hiking the scenic trails in Joshua Tree National Park is a must. Meanwhile, the Joshua Tree Music Festival features an eclectic mix of live performances from global music artists in a stunning outdoor setting. Another highlight of this historic desert town is the Palm Springs Aerial Tramway, which offers a unique perspective on the area's natural beauty.
When it’s time to dine, head to Workshop Kitchen + Bar, known for its modern American cuisine and seasonal cocktails, with an outdoor patio perfect for late-night dinners under the stars. For a taste of the nightlife, discover Reforma, a chic nightlife hotspot with Latin-inspired dishes and live entertainment. For a more relaxed vibe, Bootlegger Tiki offers imaginative cocktails in a cozy, Polynesian-inspired setting. And while in town, don’t miss VillageFest—a lively Thursday night street fair featuring live music, food, and crafts.
Good for the Great Outdoors
If you find your heart in the Great Outdoors, May might be one of the best times in the year for exploring some of the most beautiful natural landscapes in the USA. Whether you're an adrenaline junkie or just looking for a reset in fresh air and lush scenery, these outdoor-friendly cities offer adventures for everyone.
Bend, Oregon
The charming eastern Oregon town of Bend is an outdoor enthusiast's paradise. For stunning hiking trails with breathtaking views, Smith Rock State Park is the place to start. The Deschutes River is perfect for fishing and rafting adventures. For mountain biking, head to Phil's Trail, which offers a variety of trails for all skill levels. In May, Bend takes its events outdoors, with the Bend Farmers Market “springing” to life with fresh produce and local goods. There’s also the Pole Pedal Paddle, a multi-sport event that attracts athletes from all over, as well as the Bend Brews & Beyond Festival, featuring live music, food, and—of course—samplings from over 50 Oregon breweries. And there’s no better way to relax and unwind after a long day of outdoor activities in Bend than with a craft brew at any of the local breweries on the Bend Ale Trail.
Asheville, North Carolina
Adventures await in Asheville—a fantastic destination for outdoor enthusiasts. Perfect for trekkers at every level, the Blue Ridge Parkway and Craggy Garden trails both offer gorgeous views. The French Broad River is a great stop for passionate whitewater rafters and kayakers. For mountain biking, head to Bent Creek Experimental Forest, which offers 30 miles of singletrack trails with varying difficulty levels, challenging terrain, and stunning scenery. And if serenity in nature is what you seek, the North Carolina Arboretum features beautiful gardens and trails in a tranquil setting. After a day of outdoor activities, unwind with a taste of local history and wine at the incomparable Biltmore Estate.
Boulder, Colorado
Beautiful Boulder transforms into an outdoor enthusiast's paradise in May. Hike the Flatirons for stunning vista views, experience whitewater rafting on the Colorado River, and explore the Boulder Farmers Market. Enjoy stand-up paddleboarding on the Boulder Reservoir or challenge yourself to some mountain biking—both Marshall Mesa and Betasso Preserve are popular spots for beginners and advanced bikers. You can also take a scenic bike ride along the Boulder Creek Path or go rock climbing at Eldorado Canyon State Park. The Boulder Creek Fest is a must-attend event, featuring live music, food vendors, and arts and crafts. And when you’ve finally had your fill of the Great Outdoors, end your day with a craft beer and bite at any of the city’s top breweries, like Mountain Sun Pub & Brewery or Wild Provisions Beer Project.