Festivals near West Rutland, VT.

Bookstock 2026

• May. 15 - May 17, 2026
• The Green - Woodstock, VT USA

• Other / General

• FREE!!

Bookstock, the Vermont Festival of Words, features author readings; a huge used book sale; poetry; workshops; events for children; food; and other fes ....

50th ANNUAL ORFORD NH FLEA MARKET

• Aug. 1 - Aug 1, 2026
• Orford - Orford, VT USA

50th Annual Orford Flea Market Sponsored by the Orford Volunteer Fire Department, Inc. (non-profit organization) August 1st & 2nd, 2026 (Saturday & S ....

50th ANNUAL ORFORD NH FLEA MARKET

• Aug. 2 - Aug 2, 2026
• Annual Orford Flea Market - Orford, VT USA

50th Annual Orford Flea Market Sponsored by the Orford Volunteer Fire Department, Inc. (non-profit organization) August 1st & 2nd, 2026 (Saturday & S ....

65th Annual Art in the Park Summer Festival--applications available

• Aug. 8 - Aug 9, 2026
• Main Street Park - Rutland, VT USA

Chaffee Art Center's 65th Annual Art in the Park Summer Festival Aug 8 & 9 featuring fine artists & craft persons. Exhibitor APPLICATIONS available ww ....

New World Festival

• Sep. 6 - Sep 6, 2026
• Chandler Music Hall ~ Chandler Center for the Arts - Randolph, VT USA

• Music

• $25 - $50
• $50 - $100

Get ready for an unforgettable experience at the 34th Annual New World Festival! Vermont's premier Celtic & Québecois music festival. This vibrant c ....

Annual Ramblin' Roads Country Fest 2026

• Oct. 3 - Oct 3, 2026
• Bondville Fair - Winhall, USA

• Music

• $10 - $25

Ramblin’ Roads Country Fest – Vermont 2026 ?? Bondville Fairgrounds, Winhall VT ?? October 3, 2026 ?? Rain Date: October 4 ?? Doors open at Noon - 9pm ....

65th Annual Art in the Park Fall Festival--applications available

• Oct. 10 - Oct 11, 2026
• Main Street Park - Rutland, VT USA

Chaffee Art Center's 65th Annual Art in the Park Fall Foliage Festival Oct 10 & 11 featuring fine artists & craft persons. Exhibitor APPLICATIONS avai ....

Battenkill Fly fishing & Arts Festival

• Apr. 30 - May 3, 2026
• 3938 Vermont Rte 7a - Arlington, VT USA

• Music

• $10 - $25

Recently named a Vermont Signature Event, this is more than just a festival; it’s a homecoming for anyone who finds peace in the rhythm of the river a ....

Hadley Maple In April

• Apr. 25 - Apr 25, 2026
• Rockwell Street - Hadley, NY USA

Celebrate a quarter-century of sweetness at the 25th Anniversary Hadley Maple in April Festival. This beloved and long-standing community tradition ca ....

Cars, Trains, and Maple Magic: The 25th Annual Hadley Maple in April Returns!

• Apr. 25 - Apr 25, 2026
• Hadley - Hadley, NY USA

• Other / General

Celebrate spring at the Hadley Maple in April Festival, on Saturday, April 25, from 9:00 AM to 4:00 PM on Rockwell St. in Hadley, NY. This free commun ....

Cars, Trains, and Maple Magic: The 25th Annual Hadley Maple in April Returns!

• Apr. 25 - Apr 25, 2026
• Rockwell Street - Hadley, NY USA

Celebrate a quarter-century of sweetness at the 25th Anniversary Hadley Maple in April Festival. This beloved and long-standing community tradition ca ....

Spring Farmers Market

• Apr. 18 - Apr 18, 2026
• Vermont State University Randolph Campus - Randolph, VT USA

• Other / General

A market of farmers, growers, bakers, artists and craftsmen located at Vermont State University (formerly Vermont Technical College). 30 Vendors. Free ....

Area 52 Unveiled: A Night to Remember

• Jan. 31 - Jan 31, 2026
• 860 Southern Vermont Arts Center Dr - MANCHESTR CTR, VT USA

• Music

• FREE!!

Come celebrate the launch of Area 52 What is Area 52? As we navigate the ever-evolving landscape of grass and hemp-derived products, it’s essential ....

Step into Area 52: The Future is Now

• Jan. 31 - Jan 31, 2026
• Little City Cider Company - Bennington, VT USA

• Music

• FREE!!

Come celebrate the launch of Area 52 What is Area 52? As the grass industry continues to evolve, one brand that has been making waves is Area 52. Wi ....

Area 52: The Nexus of Possibilities

• Jan. 31 - Jan 31, 2026
• Area 52 - Rutland, VT USA

• Music

• FREE!!

Come celebrate the launch of Area 52 What is Area 52? Discover the Premier Online Dispensary: Area 52 In the rapidly evolving world of weed product ....

VINYL EVOLUTION - LIVE at the GRATEFUL DEN

• Nov. 14 - Nov 14, 2025
• The Grateful Den - Glens Falls, NY USA

• Music

Time to join VINYL EVOLUTION for a night to remember (National Pickle Night) for 3 sets of Rockin' Tunes, and enjoy the Grateful Den's Amazing Food an ....

Middlebury Car Show & Fall Festival

• Oct. 12 - Oct 12, 2025
• Triangle Park - Middlebury, VT USA

Join us in Middlebury for the 4th annual Middlebury Car Show & Fall Festival. Main Street will close to welcome 75 classic cars and trucks. Food truck ....

Chaffee Art Center's 64th Annual Art in the Park Fall Festival

• Oct. 11 - Oct 12, 2025
• Main Street Park - Rutland, VT USA

• Arts (Arts & Crafts)
• Community (Community / Social)
• Community (Family & Kids)
• Community (Fundraiser)
• Music

• FREE!!

64th Annual Art in the Park Fall Foliage Festival featuring fine artists and craft persons, specialty foods, kid’s activities, and musical enter ....

64th Annual Art in the Park Fall Foliage Festival

• Oct. 11 - Oct 12, 2025
• Main Street Park - Rutland, VT USA

Chaffee Art Center's 64th Annual Art in the Park Fall Foliage Festival October 11 & 12 featuring fine artists & craft persons, specialty foods, kid’s ....

Vermont Sheep & Wool Festival

• Oct. 5 - Oct 5, 2025
• Fairgrounds Road - Tunbridge, VT USA

• FREE!!
• $1 - $10

The Vermont Sheep & Wool Festival celebrates local farms and natural fibers. The event features a variety of vendors offering fleece and yarn, fiber a ....

Pasta Dinner

• Oct. 4 - Oct 4, 2025
• The Brick Church (Clarendon Congregational Church) - Clarendon, VT USA

• $1 - $10
• $10 - $25

The menu will include Penne pasta, handmade meatballs, homemade sauce, salad, rolls, dessert and drinks. Adults $12 | Kids (4-10) $6.00 - Limited Seat ....

Cider Pressing and Frost Barn Open House

• Oct. 4 - Oct 4, 2025
• Robert Frost Stone House Museum at Bennington College - Shaftsbury, VT USA

• Food / Wine / Beer

Hard cider sales and free tasting, as well as free samples of fresh-pressed juice from the Robert Frost Stone House orchard, courtesy of Watson Wheele ....

Vermont Sheep & Wool Festival

• Oct. 4 - Oct 4, 2025
• Fairgrounds Road - Tunbridge, VT USA

• FREE!!
• $1 - $10

The Vermont Sheep & Wool Festival celebrates local farms and natural fibers. The event features a variety of vendors offering fleece and yarn, fiber a ....

Puuluup (Neo-Zombie-Post-Folk)

• Oct. 3 - Oct 3, 2025
• Chandler Music Hall ~ Chandler Center for the Arts - Randolph, VT USA

• Music

• $10 - $25

Experience the Estonian zombie-folk duo Puuluup, returning to Central Vermont with their genre-defying blend of tradition and innovation. Performing o ....

Coffee & Community – National Coffee Day by Cafely

• Sep. 29 - Sep 29, 2025
• Cafely - Chelsea, VT USA

• FREE!!

As National Coffee Day approaches on September 29, it’s time to raise a mug to the brew that fuels our mornings, sparks our conversations, and connect ....