Places to Visit in May
What we love about traveling in May is that it’s more than just a trip—it’s 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. I’ve gathered my favorite May destinations and experiences, and I think you’ll enjoy them too.
1. Folsom
I thought Folsom was a charming little gem, a riverside city with a laid-back, small-town vibe, historic gold-rush architecture, a heritage of music and railroads, and a backdrop of oak-dotted hills that summed up everything I love about Northern California in one compact city!
From Sacramento, I drove about 30 minutes northeast and stayed for two days at the stylish Lake Natoma Inn. I strolled the cobbled streets of Historic Folsom, explored the fascinating Folsom Prison Museum (yes, Johnny Cash’s legendary performance looms large here), and admired vintage locomotives at the Folsom Powerhouse and Railroad Museums.
I hiked along the leafy American River Parkway, soaked up the lakeside calm at Folsom Lake, and browsed through quirky antique shops and boutiques. Evenings were spent lingering over hearty California cuisine at cozy local restaurants. Dining at Scott’s Seafood on the River, their warm sourdough bread pudding with a caramel-bourbon glaze was the showstopper!
- Highlights: Historic Folsom District, Lake Natoma, Folsom Powerhouse, Johnny Cash Trail
- Best Time to Visit: May for wildflowers, warm weather, and low crowds before summer
2. Lincoln
Lincoln is a prairie city with a laid-back, small-town vibe, graceful capitol towers, a proud pioneer heritage, and a backdrop of rolling plains that summed up everything I love about Nebraska in one compact city!
From Omaha, I drove about an hour southwest along I-80 and stayed two days at the modern Graduate Lincoln hotel. I toured the soaring Nebraska State Capitol and its art-deco murals, wandered through the Historic Haymarket District with its brick warehouses turned into cafés and galleries, and explored the excellent University of Nebraska State Museum. I strolled leafy Pioneers Park Nature Center, admired the Sunken Gardens in full bloom, and browsed quirky shops and bookstores downtown. Evenings were filled with hearty Midwestern comfort food and craft beer at local breweries. Dining at The Oven, their rich Indian-spiced bread pudding with a bourbon-cream drizzle was an unforgettable standout!
- Highlights: Sunken Gardens, Pioneers Park, Sheldon Museum of Art, Historic Haymarket District
- Best Time to Visit: May for flowers in bloom, trail weather, and outdoor dining
3. Canby
Canby is a riverside town with a laid-back, small-town vibe, fertile farmland roots, and a backdrop of green Willamette Valley hills that summed up everything I love about Oregon in one compact city! From Portland, I drove about 30 minutes south and stayed two days at the Valiant Inn.
I wandered the leafy trails of Eco Park, admired blooms at the Clackamas County Fairgrounds and Dahlia Festival, and rode the historic Canby Ferry across the Willamette River. I explored the Molalla River corridor for a taste of the outdoors, strolled through charming local shops downtown, and paused at farm stands brimming with fresh produce. Evenings brought hearty Pacific Northwest flavors at welcoming local restaurants. Dining at Wayward Sandwiches — their warm berry cobbler with a drizzle of hazelnut cream was the decadent standout!
- Drive Time from Portland: ~40 minutes south
- Highlights: Swan Island Dahlias, Molalla River State Park, Clackamas County Fairgrounds, local nurseries and cafés
- Best Time to Visit: May for soft trail weather and early blooms
4. Lexington
I thought Lexington was such a great idea for a May vacation, a rolling-horse-country city with a laid-back, small-town vibe, elegant historic districts, a proud 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. I toured stately Keeneland and its storied racetrack, explored the Mary Todd Lincoln House and Ashland (Henry Clay’s estate), and browsed the excellent 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!
- Drive Time from Roanoke: ~1 hour northeast
- Vibe: Historic, tucked-away, mountain-close
- Highlights: Washington and Lee University, Lee Chapel, Chessie Nature Trail, downtown shops
- Best Time to Visit: May for spring color, campus beauty, and clear trails
5. Kingston
I thought Kingston was a lovely riverside town with a laid-back, small-town vibe, Colonial stone houses, a proud riverfront heritage, and a backdrop of blossoming Hudson Valley hills that summed up everything I love about upstate New York in one compact city!
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!
- Drive Time from NYC: ~2 hours north
- Highlights: Stockade Historic District, Rondout Waterfront, Hudson River Maritime Museum, Trolley Line Trail
- Best Time to Visit: May for gardens in bloom, open markets, and creekside walks
6. Pelham
Pelham is a tree-lined town with a laid-back, small-town vibe, stately old homes, a proud suburban heritage, and a backdrop of blooming parks that summed up everything I love about Westchester in one compact community!
I strolled through picturesque Pelham Bay Park and the Bartow-Pell Mansion gardens in full May bloom, explored the quaint downtown with its cafés and bakeries, and admired local art at the Pelham Art Center. Spring was perfect for biking along leafy neighborhood streets, enjoying outdoor concerts and community events, and wandering through weekly farmers’ markets brimming with flowers and early produce. Evenings brought cozy dining at neighborhood restaurants. Dinner at Sergio’s Ristorante — their warm ricotta cheesecake with fresh berries was the seasonal standout!
- Drive Time from Birmingham: ~25 minutes south
- Highlights: Oak Mountain State Park, Peavine Falls, Double Oak Lake, local BBQ and antique shops
- Best Time to Visit: May for waterfall flow, mild temps, and blooming trails
7. The Berkshires
I thought the Berkshires in May were ideal! 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. I toured the Norman Rockwell Museum, explored The Mount (Edith Wharton’s stately estate), and wandered the gardens of Naumkeag, fragrant with lilacs and tulips. 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 shaking off winter. Evenings meant cozy fireside dining and farm-to-table New England flavors. Dinner at Old Inn on the Green — their rhubarb tart with fresh cream was the sweet springtime standout!
- Drive Time from Albany: ~1 hour east
- Vibe: Artistic, pastoral, thoughtfully layered
- Highlights: Pleasant Valley Sanctuary, downtown Lenox & Stockbridge, Norman Rockwell Museum, early-season concerts and gardens
- Best Time to Visit: May for blooming trails, shoulder-season prices, and quieter towns
8. Tombstone
Tombstone was a dusty desert town with a laid-back, small-town vibe, Old West saloons, a proud Wild West heritage, and a backdrop of sunbaked hills that summed up everything I love about southern Arizona in one compact city!
From Tucson, I drove about an hour southeast along I-10 and stayed two days at the historic Tombstone Monument Ranch. I toured the legendary O.K. Corral and watched the famous gunfight re-enactments, explored the Bird Cage Theatre and Tombstone Courthouse, and wandered down Allen Street lined with swinging-door saloons and vintage storefronts. I paid my respects at Boothill Graveyard, rode a stagecoach through town, and hiked the desert trails surrounding town where saguaros and ocotillo were in bloom. Evenings meant hearty cowboy fare and live country music in atmospheric saloons. Dining at Big Nose Kate’s Saloon — their warm pecan pie with a scoop of vanilla ice cream was the sweet standout!
- Drive Time from Tucson: ~1.5 hours southeast
- Highlights: Allen Street, Bird Cage Theatre, Tombstone Courthouse, Boothill Graveyard, desert trails
- Best Time to Visit: May for mild sun, fewer crowds, and early desert blooms
9. Colchester
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, a dramatic bike and walking path stretching out over Lake Champlain, explored the sandy shores of Malletts Bay, and wandered through the town’s historic green with its church spires and old stone buildings. May was perfect for kayaking on the lake, hiking through Niquette Bay State Park where trilliums and wildflowers carpeted the forest floor, and browsing local farm stands bursting with early spring produce. Evenings were filled with hearty Vermont comfort food and lakeside sunsets. Dining at Rozzi’s Lakeshore Tavern — their maple bread pudding drizzled with warm caramel sauce was the sweet standout!
- Drive Time from: Hartford ~40 min; NYC ~2.5 hrs
- Vibe: Pastoral, quiet, close-knit
- Highlights: Town Green, local farm stands, walking trails, peaceful backroads
- Best Time: Summer and fall for markets and foliage
10. Pula, Croatia
My family and I spent 6 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 Rijeka, I drove about an hour and a half south along the coast and stayed two days at the stylish Amfiteatar Hotel. I toured the magnificent Roman Arena — one of the best-preserved amphitheaters in the world — 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 at Verudela’s 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 fiery sunsets over the Adriatic. Evenings meant fresh seafood and Istrian specialties at cozy konobas. Dining at Konoba Boccaporta — their warm fritule (little sugared doughnuts) with a drizzle of rakija syrup was the sweet standout!
- Drive Time from Rijeka (fly to Rijeka or Zagreb): ~1.5–2 hours south
- Highlights: Roman Amphitheater, Brijuni Islands, Kamenjak Nature Park, seaside promenades
- Best Time to Visit: Late spring and early autumn for warm water and fewer crowds
Conclusion
Somewhere between the desert hush of Tombstone and the riverside calm of Kingston, I realized what these places had in common. They weren’t calling for attention. They were waiting to be noticed. May is like that too, tucked between spring’s chaos and summer’s rush, full of light, bloom, and space to move at your own speed.
I walked trails where waterfalls had just reawakened. I sat on porches warmed by the first steady sun. I tasted meals that still remembered the earth. And in every town, whether it was rooted in gold, river, prairie, or pine. I found a rhythm that matched my own quiet shift into something new.
These are the places that remind you to stretch, to linger, to begin again without hurrying. If you need a trip that gives more than it takes, May is waiting. So are these towns.
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.
