September 2025 in Southern Vermont

Author

So Vermont
August 29, 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

New England Street Food Fest

September 6th | Brattleboro

8th Annual Street Food Festival - Brattleboro Vermont

Event in Brattleboro, VT by New England Street Food Fest and Brattleboro Reformer on Saturday, September 6 2025 with 831 people interested and 41 people going. 8 posts in the discussion.

www.facebook.com/events/1234213808250979

Roger Clark Miller & Mythless

September 6th | Newfane

SOLO GUITAR: Roger Clark Miller & Mythless - Music At Union Hall

The first collaboration between Newfane's Music at Union Hall and BMAC: Please join us in welcoming two boundary dissolving pioneers of guitar music for our September show. Roger Clark Miller and Mythless will deploy their unique set-ups in Union Hall for a performance that's sure to be unforgettable.

musicatunionhall.com/show/solo-guitar-roger-clark-miller-mythless

Whoopie Pie Festival

September 13th | Rutland

Rutland Whoopie Pie Festival

Center Street & Merchants Row | 12-4PM

Save the date for the 4th annual Rutland Whoopie Pie Fest on
Saturday September 13th 2025!

The fourth annual Rutland Whoopie Pie Festival will be an all-day extravaganza with something for everyone! Enjoy the day with music, performances, activities, and diverse foods.

What Doth Rumble Music Fest

September 13th | White River Junction

WHAT DOTH RUMBLE 2025 | mainstreetmuseum

Music Festival Music workshops Vendors

www.mainstreetmuseum.org/wdr25

Wine and Improv Night @ Bennington Theater

September 18th | Bennington

Wine & IMPROV

Get ready for a night of hilarious improvisation where the only script is spontaneity! Join us for an interactive evening of improv games led by the incredible Stephanie Phelan, a seasoned performer and director.

tickets.benningtontheater.org/event/wineimprov-5ili41?eventId=68a37bbbbd10b504a5c5bebe

Vermont Wine & Harvest Festival

September 19th-20th | West Dover & Wilmington

Home | VT Wine Festival

Wine Stroll and Soup Contest 
Friday, September 19, 4:00 pm-7pm - Historic Downtown Wilmington 
16th Annual Vermont Wine & Harvest Festival
Grand Tasting & Artisan Expo
Saturday, September 20, 11am - 5pm - Mount Snow Resort, West Dover

https://www.vtwinefest.com

Brattleboro Museum & Arts Center Gala

September 20th | Brattleboro

BMAC Gala 2025 | All Together Now — Art Loves Company

Delicious appetizers, cocktails, and desserts | Exciting silent and live auctions | Special performance by dazzling 18-year-old singer/songwriter Emily Margaret of Guilford, Vermont | Recognition of our very own chief installer, Tim Allen—a beloved, behind-the-scenes art hero who has helped bring about every BMAC exhibit for over 20 years

www.artlovescompany.org/bmac-gala-2025-all-together-now

Stone Skipping Festival

September 20th | North Bennington

Peru Fair

September 27th | Peru

THE PERU FAIR

Fabulous Pig Roast, Music & Family Entertainment, Vermont Crafts, Cloggers, Antiques & Art Exhibits, Vermont Artisans Demos, Face Painting & Magicians, Food & Vermont Fare, Baked Goods, & Fun for Everyone!

www.perufair.org

Concerts @ StoneChurch

All Month Long | Brattleboro

UPCOMING EVENTS | Stone Church, Brattleboro VT — Your Site Title

Upcoming Events | Stone Church, Brattleboro VT. Experience the best live music in Brattleboro at Stone Church VT. Check out our event calendar for upcoming shows!

stonechurchvt.com/events#/events

Outdoor

Lake Lowell State Park in Londonderry

This one can be hard to find(don’t listen to your GPS!) but it’s a great hike with a lot of variety. Lake views, forest trails, a revolutionary-war-era cemetery, and an abandoned summer camp, all at one park!

Find it off route 11, and don’t approach from Little Pond Road! Take Route 11 to Lowell Lake Road.

Dining

Valley View Saloon in West Dover

This secluded spot was a treat. We went on a Thursday and had the creekside outdoor section all to ourselves. Pictured: “Psycho Chicken” Sandwich with Coleslaw.

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