10 Best Underrated Places to Visit in May
What we love about traveling in May is a chance to pause and breathe between the busyness of spring and the rush of summer. Without the peak-season crowds, we found time to slow down, get curious, and let each place reveal its charm in its own way. We didn't need to have reservations for the most famous attractions, found great deals on hotels and public transportation wasn't overcrowded. I’ve gathered my favorite May destinations and experiences on my four week road trip this month, and I think you’ll enjoy them too.
1. Folsom, CA
This month turned out to be an incredible time to explore Folsom, CA because you'll get golden sunshine, trails lined with spring wildflowers, and the sparkling calm of Folsom Lake before the summer crowds.
After flying into Sacramento International (SMF), I drove 40 minutes and spent four days at 3-star Hilton Garden Inn Folsom, exploring boutique shops, lakeside parks, and the Saturday Farmers Market.
I loved my bike ride along the American River Parkway, watching kayakers glide past, and dining outdoors in Historic Folsom. You can also visit the Folsom Prison Museum, watch the sunset over the lake, and have great burgers at Plank Craft Kitchen + Bar.
- Average temperature: 50°F – 76°F (10°C – 24°C)
- Map & Directions
My highlight was sitting outside and listening to live music drifting through the plaza in Folsom.
2. Lincoln, NE
May is an incredible time to explore Lincoln, Nebraska. you get sunny afternoons, blooming parks, and lively downtown streets made the city shine without the crowds. You can stroll through the Sunken Gardens, catch live music on a patio in the Historic Haymarket, and dine outdoors with the scent of sizzling Midwest barbecue in the air.
I timed my trip for the Lincoln Marathon & Half, which fills the streets with energy and celebration.
Flying into Lincoln Airport (LNK), I drove just 15 minutes and spent four days at the stylish Kindler Hotel, browsing indie shops, and cozy cafés.
You can also check out Sheldon Museum of Art and Historic Haymarket District.
- Average temperature: 53°F – 71°F (12°C – 22°C)
- Map & Directions
3. Canby, OR
This month turned out to be an incredible time to explore Canby, Oregon — soft sunshine, blooming fields, and the start of river season made this Willamette Valley town sparkle without the summer rush. I loved my walk along the Molalla River State Park trails, crossing the historic Canby Ferry, and dining outdoors downtown with the scent of fresh flowers carried in the breeze.
I timed my trip for the Canby Wine, Food & Brew Festival, which brings together local vintners, craft brewers, and chefs, and the Canby Farmers Market, overflowing with fresh produce, flowers, and artisan goods.
Flying into Portland International Airport (PDX), I drove 35 minutes and spent a day at Motel 6 Canby, OR, exploring nurseries, riverside parks, and the charming shops in downtown Canby.
You can check out Clackamas County Fairgrounds and Dahlia Festival, ride the historic Canby Ferry across the Willamette River, and explore the Molalla River corridor.
- Average temperature: 43°F – 66°F (6°C – 19°C)
- Location: Map & Directions
4. Lexington, KY
Lexington is one of the best places to visit in May. Why? In the spring, Lexington, KY has a laid-back, small-town vibe, elegant historic districts, a proud horse-and-bourbon-and-bluegrass heritage, and a backdrop of white-fenced pastures that summed up everything I love about Kentucky in one compact city!
From Frankfort, I drove about half an hour southeast and stayed two days at the boutique 21c Museum Hotel. You can gour stately Keeneland and its storied racetrack, explore the Mary Todd Lincoln House and Ashland (Henry Clay’s estate), and browse art galleries and exhibits at the University of Kentucky Art Museum. I strolled through the Arboretum State Botanical Garden, joined a behind-the-scenes distillery tour at Woodford Reserve, and soaked in the energy of the Distillery District. Evenings were all about hearty Southern cooking and craft cocktails. Dining at Carson’s Food & Drink... their bourbon bread pudding with vanilla crème anglaise was the sweet highlight!
- Average temperature: 56°F – 75°F (13°C – 24°C)
- Location: Map & Directions
5. Kingston, NY
May turned out to be an incredible time to explore Kingston, New York with warm sunshine, blooming riverfront parks, and the start of boating season made this Hudson Valley gem glow without the peak summer crowds. I loved my stroll through the Rondout waterfront, watching sailboats drift along the Hudson, and dining outdoors on the historic Strand with the scent of wood-fired pizza wafting through the air.
From New York City, I drove about two hours north along the Hudson and stayed two days at the historic Hotel Kinsley. I wandered through the Stockade District with its 17th-century Dutch architecture, explored the Hudson River Maritime Museum and Rondout waterfront, and admired contemporary works at local galleries. May was perfect for strolling the bluffs of Hasbrouck Park, browsing the outdoor farmers’ markets bursting with fresh produce and flowers, and taking a scenic boat cruise on the Hudson. Evenings meant cozying up in inventive farm-to-table restaurants. Dining at Ship to Shore... their seasonal strawberry shortcake with fresh whipped cream was the sweet standout of spring!
- Average temperature: 48°F – 69°F (9°C – 20°C)
- Location: Map & Directions
6. Pelham, AL
This month turned out to be an incredible time to explore Pelham, Alabama with gentle spring sunshine, blooming dogwoods, and the start of concert season made this Birmingham-area town come alive without the heavy summer crowds. I loved my hike through Oak Mountain State Park, spotting wildlife along shaded trails, and dining outdoors with smoky Southern barbecue perfuming the air.
I timed my trip for the Pelham Palooza Festival, which brought local vendors, live music, and family fun to town, and the Oak Mountain Spring Bird Walks, where naturalists guided visitors through forests alive with songbirds.
Flying into Birmingham-Shuttlesworth International Airport (BHM), I drove 25 minutes and spent four days at the relaxing Hampton Inn & Suites Pelham, exploring nearby wineries, cozy cafés, and the Saturday farmers market.
- Average temperature: 61°F – 81°F (16°C – 27°C)
- Location: Map & Directions
Catching a live show under the stars at the Oak Mountain Amphitheatre was my personal highlight.
7. The Berkshires
I thought the Berkshires in May were ideal and one of the best places to visit when I moved to New York. I enjoyed this rolling hill country with a laid-back, small-town vibe, Gilded Age mansions, a proud artistic heritage, and a backdrop of blooming meadows and mountain ridges that summed up everything I love about western Massachusetts in one compact region!
From Boston, I drove about two and a half hours west along the Mass Pike and stayed three days at the historic Red Lion Inn in Stockbridge. You can tour the Norman Rockwell Museum, explore The Mount (Edith Wharton’s stately estate), and visit the gardens of Naumkea. May was perfect for hiking Monument Mountain and strolling through the Berkshire Botanical Garden, while downtown Great Barrington and Lenox buzzed with cafés, bookstores, and galleries. Dinner at Old Inn on the Green... their rhubarb tart with fresh cream was the sweet springtime standout!
- Average temperature: ~ 45 °F – 72 °F (7 °C – 22 °C)
- Location: Map & Directions
8. Tombstone, AZ
May in Tombstone, Arizona meant warm desert sunshine, blooming cactus flowers, and lively reenactments on historic Allen Street made the Old West town come alive without the peak summer heat. I loved my stroll past wooden boardwalks, watching costumed gunfighters stage showdowns, and dining outdoors with mesquite-grilled steak perfuming the evening air.
- Average temperature: 55°F – 82°F (13°C – 28°C)
- Location: Map & Directions
9. Colchester, VT
I thought Colchester was a charming little gem in May — a waterfront town with a laid-back, small-town vibe, deep colonial roots, a proud maritime heritage, and a backdrop of leafy New England hills that summed up everything I love about Vermont in one compact community!
From Burlington, I drove just fifteen minutes north and stayed two days at the welcoming Inn at the Round Barn Farm. I strolled along the Colchester Causeway over Lake Champlain, explored the sandy shores of Malletts Bay, and wandered through the town’s historic green. May was perfect for kayaking on the lake, hiking through Niquette Bay State Park, and browsing local farm stands bursting with early spring produce. Dining at Rozzi’s Lakeshore Tavern, their maple bread pudding drizzled with warm caramel sauce was the sweet standout!
- Average temperature: 45°F – 65°F (7°C – 18°C)
- Location: Map & Directions
10. Pula, Croatia
We spent two wonderful weeks in Pula, Croatia, a seaside city with a laid-back, small-town vibe, ancient Roman ruins, a proud seafaring heritage, and a backdrop of Adriatic blue that summed up everything I love about Istria in one compact city!
From Trieste, we drove about an hour and a half south along the coast, toured the magnificent Roman Arena, explored the Temple of Augustus and Arch of the Sergii, and strolled the marble-paved streets of the Old Town.
May was perfect for wandering along the waterfront promenade, relaxing on pebble beaches, and savoring the first hints of summer without the high-season crowds. I browsed local markets brimming with olive oils, truffles, and wines, and soaked in the sunsets over the Adriatic.
- Average temperature: 53°F – 70°F (12°C – 21°C)
- Location: Map & Directions
Conclusion
I think May is a wonderful time to travel, just before the summer rush. You can stay longer because the prices are lower. At the same time, many festivals take place in May. I included my absolute favorite places to visit this month and hope you enjoy them too.
Booking Checklist
1. Book Your Flight - I use Expedia because I like their mobile app with my itinerary. They've helped me re-book flights on many occasions. Once you reach their Gold tier, support is especially good.
2. Book Your Hotel - I use Booking.com or Expedia, depending on my destination.
3. Book Your Rental Car - I use Expedia.
4. Book your tours on Viator or Get Your Guide.
