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The Best Fall Festivals To Enjoy In Fairfield County

Picture of Katherine Schweizer
Updated: 9 February 2017
As the heat of summer subsides and the back-to-school frenzy fades behind us, it’s time to take a breath and savor Connecticut’s autumn glory. Even though Connecticut is the third smallest state in the nation, it is home to family-friendly festivals and fall in Fairfield County is the perfect time of year to experience them. Here are our top five festival picks in Fairfield in the fall.
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Fall Festival to Benefit Animals

What started out as a small dog walk with a few booths has grown into the Stratford Animal Rescue Society’s Annual Festival to Benefit Animals. As their largest fundraiser, this event features educational speakers, music, entertainment, food, over 90+ people and pet vendors, a microchip clinic, large silent auction, contests, pet adoptions and more. All proceeds go towards helping animals throughout most of the year. STAR stays true to its mission to facilitate and expedite the adoptions of homeless animals into loving homes, as well as provide food, medical care and necessities for the animals impounded at the Stratford Animal Control Facility. Come out in early October and be a part of the scene in the one-mile dog walk down Main Street.

Paradise Green Park, Huntington Road, Stratford, CT, USA, +1

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Bruce Museum’s Outdoor Arts Festival

Come and enjoy the Bruce Museum’s Annual Outdoor Arts Festival the second weekend of October. Featuring dozens of artists from all over the country, this nationally recognized event lures artists and art lovers from all over North America, from California to Canada and beyond. The purpose of this festival is to foster an appreciation of, and increase an interest in, the fine arts. There are demonstrations, family art activities, live music and food. Juried exhibitors specialize in ceramics, jewelry, wood, metalwork, leather, paper arts and glass, just to name a few, and all of them are available for purchase.

Bruce Museum, 1 Museum Drive, Greenwich, CT, USA, +1 203 869 0376

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Earthplace Festival Weekend

Organized by Earthplace, The Nature Discovery and Environmental Learning Center, and taking place the first weekend of October, this two-day event has something for everyone. There is the Woodside Bash, an adult-only event where guests can enjoy cocktails, dinner under the stars and live music. They also have the opportunity to ride a mechanical bull, stroll down a haunted trail and relax around a fire pit. For the whole family, head down to The Earthplace Festival, where activities include jumping into a corn pool (yes, corn), a natural obstacle course, pine climb, apple slingshot, and much more. This event is the largest annual fundraiser for Earthplace and proceeds benefit scholarships, nature education programs, and community outreach.

Earthplace, 10 Woodside Lane, Westport, CT, USA, +1 203 557 4400

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Plasko’s Farm Scarecrow Festival

Emjoy fun-filled family day at Plasko’s Farm, at their Annual Scarecrow Festival on the first Sunday of October. Founded in 1925, Plasko’s Farm is one of the oldest working farms in the state. The Scarecrow Festival began in 1998 as a way for people to become familiar with the last working farm in Trumbull. There is something for everyone at this family-friendly festival, from horse rides to face painting to games and more. This event also features handcrafts like candle making, a caricature artist, community booths, the decorating of scarecrows, pumpkins and fall decor, and of course food, including apple cider, doughnuts, ice cream and sandwiches. The festival is free to attend, but there is a small fee for the Monster Mystery Maze. Get lost in the maze’s 1.5 miles of twists and trails while supporting a great cause, as a portion of each admission is donated to St. Vincent’s Swim Across the Sound charity for cancer research and education.

Plasko’s Farm, 670 Daniels Farm Road, Trumbull, CT, USA, +1 203 268 2716

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Festival of Trees and Wesley Village Craft Fair

Kick the holiday season off in style at the Annual Festival of Trees and Wesley Village Craft Fair. Shop for Christmas gifts at the Wesley Village Craft Fair, or try your luck at winning one of the beautifully decorated, themed Christmas trees donated by local businesses, organizations and individuals. The Festival of Trees and Wesley Village Fair benefits Volunteer Caregivers at TEAM and activity programs for seniors at Wesley Village. The event features a Holiday Crafts Fair, with more than 50 vendors offering a variety of unique gifts and handmade crafts, and a Holiday Bake Sale. Come out and enjoy all this festival has to offer November 19th and 20th.

Wesley Village, 580 Long Hill Avenue, Shelton, CT, USA, +1 203 225 5000