October 2025 in Southern Vermont

Welcome to your local update! Here's everything happening around Wilmington and southern Vermont this month.

The air is crisp, the mountains are ablaze with vibrant color, and the scent of pumpkin spice is definitely in the air! October in Southern Vermont is truly magical, and we’re absolutely thrilled to bring you a packed calendar of events that celebrate everything we love about this glorious season.

From bustling harvest festivals and unique craft markets to spirited Oktoberfest celebrations and family-friendly farm fun, there's something for everyone to enjoy amidst our breathtaking fall foliage. So grab your flannel, sip your cider, and let’s dive into what’s happening this month!

Reminder: For weekly and monthly recurring events, check out our recurring events post here.

Festivals & Fairs

Danby Harvest Festival
When: October 4 – 5, 2025
Where: Danby, VT - 279 US 7 A quintessential Vermont country fair, this festival offers live music, festive food, an array of craft vendors, pony rides, and activities for the whole family. It's a joyful celebration of the harvest season that you won't want to miss! Learn more here

Mount Snow Oktoberfest
When: October 4 and October 11, 2025
Where: West Dover, VT - Mount Snow Resort Raise a stein and get into the Oktoberfest spirit with Mount Snow's lively take on the classic festival. Enjoy free admission, traditional German bierhalles with a diverse selection of beers and ciders, and authentic Oktoberfest fare. Prost! Find out more

Newfane Heritage Festival
When: October 11 – 12, 2025
Where: Newfane, VT - Newfane Village Experience a classic Vermont fall festival with a juried arts and crafts show, delicious local specialty foods including famous apple pie, children's activities, and live entertainment, all set against a backdrop of peak fall foliage. It's truly picture-perfect Vermont! Discover more

Oktoberfest at Stratton Mountain
When: October 12, 2025
Where: Stratton Mountain, VT - Stratton Mountain Resort Keep the HarvestFest weekend going with this traditional Oktoberfest celebration featuring lively music, exciting stein hoisting and keg toss competitions, and delicious beer and brats. The mountain air makes the perfect backdrop for this festive event! Get the details

4th Annual Bennington Harvest Fest
When: October 18, 2025
Where: Bennington, VT - Downtown Bennington (Main Street and School Street) Immerse yourself in the heart of autumn at this vibrant downtown celebration featuring over 100 craft and food vendors, lively music across multiple stages, and a dedicated Kid Zone in Merchants Park. It's the perfect way to embrace the fall foliage and community spirit. Explore the festival

Gilfeather Turnip Festival
When: October 25, 2025
Where: Wardsboro, VT Celebrate Wardsboro's famous Gilfeather Turnip with delicious Gilfeather soup, fresh turnips, seeds, and charming souvenirs. This unique, volunteer-run festival is a true taste of local tradition and community spirit – you won't find anything else quite like it! Visit the library's site

Arts & Culture

Southern Vermont Art Center Fall Craft Market
When: October 4 – 5, 2025
Where: Dorset, VT - Southern Vermont Arts Center Immerse yourself in the creativity of the region's finest artisans at this exquisite fall craft market. Discover unique handmade gifts and treasures amidst the height of Vermont's stunning foliage, with free admission for all. Plan your visit

Readsboro Harvest Craft Festival
When: October 25, 2025
Where: Readsboro, VT - Readsboro Community Library Explore unique handmade creations from talented local crafters at this festive fall market. Find special gifts and support local artists in the charming setting of the Readsboro Community Library. See more here

Live Performances

Comedian Bob Marley Live
When: October 10, 2025
Where: Brattleboro, VT - Latchis Theatre Prepare for a night of side-splitting laughter as renowned comedian Bob Marley takes the stage at the historic Latchis Theatre. This is an evening of entertainment you won't want to miss – get ready to laugh until your sides ache! Get your tickets

Boston States Fiddle Camp Concert
When: October 26, 2025
Where: Marlboro, VT - Potash Hill Immerse yourself in the rich traditions of Scottish music and culture with a world-class performance featuring fiddles, bagpipes, Gaelic song, and step dancing. This concert is the grand finale of an immersive music weekend, promising an unforgettable experience. Discover the music

Ali McGuirk
When: October 2, 2025
Where: Bennington, VT - Bennington Theater
Vermont's own powerhouse vocalist, Ali McGuirk, brings her soulful, genre-defying sound to the Bennington Theater. Prepare for a night of rich, atmospheric music that blends vintage soul, R&B, and modern grooves. Grab your tickets!

Sean Rowe
When: October 2, 2025
Where: Brattleboro, VT - Stone Church
Enjoy an intimate evening of powerful folk and blues with singer-songwriter Sean Rowe, known for his resonant voice and captivating storytelling. It's a perfect night to connect with raw, authentic music. More details here.

Shawn Mullins
When: October 8, 2025
Where: Brattleboro, VT - Stone Church
Don't miss the chance to see Grammy-nominated artist Shawn Mullins live, as he brings his soulful voice and acclaimed songwriting to the Stone Church stage. Expect an evening of heartfelt melodies and engaging lyrics. Secure your spot!

Kalbells
When: October 10, 2025
Where: Brattleboro, VT - Stone Church
Dive into the eclectic and experimental pop sounds of Kalbells, offering a unique and mesmerizing musical journey. This performance promises to be an innovative and unforgettable experience. Experience the sound.

Ensemble Amphion Baroque: Grace and Grandeur
When: October 25, 2025
Where: Brattleboro, VT - Brattleboro Museum & Art Center
Experience an evening of exquisite classical music as Ensemble Amphion Baroque performs masterpieces from France and Germany. This performance will fill the museum with grace and grandeur, creating a truly memorable cultural experience. Learn more.

Boojum
When: October 31, 2025
Where: Brattleboro, VT - Stone Church
Celebrate Halloween with Boojum, delivering a night of energetic music and a vibrant atmosphere. Get ready to dance until the witching hour in this spirited performance! Get ready to dance!

Family Fun

John Deere Fever & Vermont Products at Boyd Family Farm
When: October 11 – 12, 2025
Where: Wilmington, VT - Boyd Family Farm, 125 East Dover Road Enjoy a family-friendly fall outing with a display of farm tractors, plenty of seasonal decorations, and the chance to order your holiday wreaths, centerpieces, and trees. It’s a true celebration of Vermont's agricultural charm and perfect for all ages! Visit Boyd Family Farm

Family Fall Fest
When: October 18, 2025
Where: Dorset, VT - Dorset Village Library Celebrate the autumn season with delightful games, creative crafts, and festive snacks on the library lawn. Halloween costumes are highly encouraged for a day of free, family-friendly fun that everyone will adore! See library events

Phew! What a lineup for October! We hope this guide helps you make the most of the glorious fall season in Southern Vermont. Whether you're seeking cultural enrichment, festive family fun, or just a good old-fashioned harvest celebration, our region is brimming with opportunities to create unforgettable memories.

Enjoy the vibrant foliage, the crisp air, and all the wonderful community spirit that makes Southern Vermont so special. We'll see you out there!

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