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August 2025 in Southern Vermont
So Vermont
August 01, 2025
Welcome to your local update! Here's everything happening around Wilmington and southern Vermont this month.
Reminder: For weekly and monthly recurring events, check out our recurring events post here.
Events
Summary Table
Date(s) | Town / Area | Event / Activity |
|---|---|---|
Jul 25–Aug 3 | Wilmington/Dover | Vermont Blueberry Festival |
Aug 1 | Brattleboro | Gallery Walk |
Several Sundays/Wed | Dover | Summer Concert Series at Dover Park |
Thursdays into Aug | Brattleboro | Food Truck Roundup at Retreat Farm |
Aug 16 | Brattleboro | Ramble Bike Ride |
Aug 9 & 14–17 | Bennington | Bennington Battle Day Weekend |
Aug 14 | Bennington | Hemming’s Cruise‑in & Live Music |
Aug 30 | Bennington | Garlic Town, USA Festival |
Aug 30 | Manchester Center area | Country Festival on the Farm |
All August | Wilmington & region | Molly Stark State Park hiking, camping |
Vermont Blueberry Festival
If you’re reading this on Friday, August 1st, then Blueberry festival is already under way. It started last week, and will be finishing up this weekend.
Marlboro Music Festival
Saturday, August 2nd
Bennington Battle Day Weekend
Celebrated over August 9 and August 14–17, 2025, culminating in the official state holiday on Saturday, August 16. Includes:
Basket Bingo (Aug 9 evening)
Cruise‑in Car Show & Live Music (Aug 14, 5–8 pm downtown)
Cornhole Tournament, Fireman’s Lunch, Chicken BBQ, Vegas Night, Kids Day, and the Parade on Aug 17 at 12:30 pm
Battle reenactment encampment, free admission at Bennington Battle Monument (Aug 16 & 17)
5K road race on Aug 16 at 8:30 am followed by battlefield tours near Walloomsac, NY
Garlic Town, USA
Downtown Bennington
Saturday, August 30, 2025: Vermont’s annual garlic festival. Over 135 vendors focusing on garlic growers, local foods, artisan shopping, live music, and family fun in Bennington’s downtown.
Concerts on the Farm at Earth Sky Times
August 3rd
Glen David Andrews
More info: https://earthskytime.com/2025-summer-lineup/2024/7/21/glen-david-andrews-6l324
August 17th
SAHA GNAWA
More info: https://earthskytime.com/2025-summer-lineup/2025/8/17/saha-gnawa
August 31st
Billy Wylder's Moonshine
More Info: https://earthskytime.com/2025-summer-lineup/2024/9/1/billy-wilder-moonshine-ct43a
Manchester Music Festival
Green Mountain Bluegrass Festival
Manchester | August 14th-17th
Bennington Food Truck Festival
August 16th
Bondville Fair
Winhall | August 22-24
Concerts at Stone Church
Brattleboro
Outdoor
Ramble Bike Ride
Brattleboro
Saturday, August 16, 2025: A supported 15-, 30-, or 50‑mile scenic ride through farmland, covered bridges, and rolling hills. Hosted at Retreat Farm.
Dining
Kipling’s Tavern in Brattleboro
Based on our experiences having been to Kipling’s twice, we can say with some confidence that it is a Brattleboro local favorite. Not only is it always packed, but the staff seems to be very used to starting a waiting list for seating.
Awesome wrap around bar, delicious pub food with some locally sourced ingredients, and a great rotating selection of beers.
If any of that is up your alley, check out Kiplings.
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