May 2026

Author

So Vermont
May 01, 2026

May in Southern Vermont

The leaves are back. So is everyone's social calendar.

May is when southern Vermont wakes up all at once. The galleries stay open late, the trail shoes come back out, food festivals start making ambitious promises, and every town seems to remember it has a bandstand, a theater, a museum, or a slightly muddy field worth gathering in.

This month, the trick is not finding something to do. The trick is choosing.

Brattleboro

Stone Church keeps the Brattleboro music calendar loud, varied, and slightly unpredictable, which is exactly what it is for.

If you want the full month, start with Stone Church's own calendar. The venue tends to add and update shows as the season fills in.

BMAC has the cleanest May arts lineup in Brattleboro: late museum hours, hands-on making, and a members' evening with artist Michaela Harlow.

If you have been meaning to do Gallery Walk "one of these months," May is the month it stops sounding theoretical.

Gallery Walk returns for the season with galleries, maker energy, downtown wandering, and the reliable feeling that Brattleboro has more going on per square block than should be physically possible.

Putney

Next Stage has a strong May, especially if your ideal night out involves actual listening rather than shouting over a bar.

Putney in May is sneaky-good: dinner, a show, and then the short drive home with the windows cracked because you are pretending it is fully summer.

Bennington

Bennington Theater's May calendar is compact, local, and nicely varied: drag, trivia, improv, and a low-cost theater weekend.

This is the rare venue where you can make an argument for going twice in one week and not feel irresponsible.

Bennington Museum is leaning into regional history, folk tradition, and a little well-timed Vermont scandal.

The end-of-month opening of Vermont Vice is the one to watch. It has the title of an exhibit people will claim they are seeing for "historical reasons," which is how you know it will be fun.

Bennington starts the month with a homebrew street-festival situation and closes the big Memorial Day stretch with Mayfest. That is a respectable civic arc.

North Bennington

Spring ephemerals, old grounds, and an excuse to get outside before the day gets away from you. Rain, shine, or snow, because Vermont likes to keep legal options open.

Manchester

Manchester gets Memorial Day weekend started with tastings, tours, wine dinners, chef-led events, a Grand Tasting, and enough well-plated optimism to make you briefly believe you are the kind of person who plans weekends elegantly.

Arlington

This one technically starts the evening before May, but the festival's main May dates bring the Bamboo Derby, art, river culture, brews, and a very good excuse to spend time around Arlington and the Battenkill.

Townshend

This is a fundraiser for Grace Cottage at Big Picture Farm, which means the pitch is simple: baby goats, a good cause, and almost no moral downside. Sometimes an event knows exactly what it is.

Run, walk, roll, stroll, or push a stroller. The 17th annual Grace Cottage 5K is low-pressure, community-minded, and supports a hospital people around here genuinely rely on.

Wilmington

Pettee keeps the Wilmington calendar quietly useful: books, families, and the sort of local programming that makes a small town feel like it is taking care of itself.

Have an event to share? Reply to this email or send it to [email protected]. Know someone who'd enjoy this? Forward it along.