Spring festivals, food, music across Vermont
Here are 18 events across Vermont May 15-30...
18 things to do in May in Vermont
From hot air balloons floating over the Upper Valley to goat lunches, mountain hikes, food festivals, live music, and Memorial Day celebrations, the next few weeks are packed with events across Vermont. Whether you’re looking for family-friendly fun, outdoor adventures, local food and craft fairs, or small-town community gatherings, there’s something happening in nearly every corner of the region this spring.
Here are 18 events across Vermont May 15-30:
- 🎈 Experimental Hot Air Balloon Festival
Post Mills, May 15–17
Balloon launches, community dinners, and family-friendly festivities at Post Mills Airport.
More info - 🎶 Music on the Mountain
Ludlow, May 16
Community-powered live music festival celebrating connection and recovery.
More info - 🌸 Jamaica Mayfest
Jamaica, May 16
Maypole ceremony, yoga, pollinator workshop, live music, arts, and a community picnic.
More info - 🛒 Jericho Farmers Market Opening Day
Jericho, May 21
Opening day celebration featuring local vendors and live music.
More info - 🍷 Manchester Vermont Food & Wine Festival Manchester
May 22–24
Wine tastings, chef showcases, artisan vendors, and live music at the Equinox Resort.
More info - 🎨 Mayfest Arts & Crafts Festival
Bennington, May 23
Downtown street fair with crafts, food vendors, and entertainment.
More info - 🎸 Memorial Day Weekend Concert with Saints & Liars
Stratton, May 23
Free live music performance at Stratton Mountain Resort.
More info - 🥾 Hike with a Guide
Stratton, May 24
Free guided hike up Stratton Mountain followed by a gondola ride back down; moderate 2.14-mile hike beginning at 9 a.m.
More info - 🐶 Doggie & Me 5K Run
Stratton, May 25
8:30 a.m. race at Stratton Mountain Resort benefiting the Windham County Humane Society; first 150 participants receive matching T-shirts.
More info - 🐑 Marlboro Morris
Ale Marlboro, May 25
Vermont Folk dancing, bells, ribbons, musicians, and roaming performances throughout Windham County.
More info - 🍺 Brew the 802
South Burlington, May 25
Craft beer festival featuring Vermont breweries and live entertainment.
More info - 🛠️ Underhill Ironworks Memorial Day
Open Studio Underhill, May 25
United States Giant welded sculptures, mountain views, and Vermont Crafts Council artists on display.
More info - 🎖️ Memorial Day Celebration at Roaring Brook Park
Barton, May 25
Pulling events, demolition derby, food vendors, baseball tournament, and family activities.
More info - 🇺🇸 Memorial Day Weekend in Wilmington
Wilmington, May 24–25
Memorial Hall tours, BBQ, parade, and remembrance ceremony.
More info - 🥾 Hiking 101
Waterbury Center, May 27
Beginner-friendly hiking workshop hosted by the Green Mountain Club.
More info - 📚 Someday Book Club
Waitsfield, May 28
Community book club for women gathering at Someday Boutique. They will be discussing “Strangers” by Belle Burden.
More info - 🏳️🌈 Essex Pride Weekend
Essex Junction, May 29–31
Celebration with live music, vendors, food, drag story hour, comedy show, a festival, and more.
More info - 🐐 Lunch with Baby Goats
Walpole, NH, May 30
NH Family-friendly lunch event with baby goats and farm fun.
More info
