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  • Middlebury Pride

    Downtown Middlebury

    Inclusive and family-friendly parade down Main St., followed by a festival in the green! Learn more here.

    Free

  • Harvest Music Series: Liz Reedy

    Champlain Orchards 3597 VT-74 W., Shoreham, VT

    Liz Reedy: Liz Reedy is a versatile musician and songwriter based in the mountains of Killington, Vermont. Known for her soulful acoustic performances, commanding vocals, and deep roots in the local music scene, Liz blends genres to create an authentic, engaging sound that resonates with audiences of all kinds. Join us at the orchard for […]

  • Parent Playdate

    The Congregational Church of Middlebury 2 Main Street, Middlebury, VT, United States

    Are you the parent of a child age 4 or under? Join other new parents for a time of fellowship, discussion and dinner once a month, usually the second Saturday from 4:00- 6:00 pm. A delicious homemade dinner is provided, and children are lovingly cared for in the nursery. RSVP to Pastor Elizabeth Gleich.

    Free

  • Middlebury Car Show & Fall Festival

    Triangle Park Main St. and Merchants Row, Middlebury, VT, United States

    Join us for the 5th Annual Middlebury Car Show & Fall Festival. Main Street will close to welcome 75 vehicles for a day of family-friendly fun in the heart of downtown. Enjoy food trucks, 30+ vendors, music, children’s activities, and more while exploring one of Vermont’s most vibrant downtowns. Brought to you by the Addison County […]

    Free

  • 39th Annual Ripton Ridge Run

    Former Ripton Elementary School 753 Lincoln Rd., Ripton, VT, United States

    5K run, 10.5K run and non-competitive 5K Fun Walk on scenic roads. Registration fee includes long-sleeved t-shirt, lunch and raffle. Hosted by Friends of Ripton Students Inc., this fundraiser benefits Ripton students of all ages. Register online before Oct. 10 or in person from 11 a.m. – noon on race day.

  • Harvest Music Series: Bird Mountain String Band

    Champlain Orchards 3597 VT-74 W., Shoreham, VT

    Bird Mountain String Band: Family old-time and bluegrass band from a small farmstead in Vermont. Join us at the orchard for a day of apple picking and great music! The Cider Garden will also be open for full cider pours and tasting flights, cider slushies, charcuterie boards, s'mores, soft pretzels, and so much more. Gather […]

  • Live Music: Justin Lapoint

    Yates Orchard 1074 Davis Rd., Hinesburg, VT

    Bring a picnic, enjoy a Dreamee and relax in the orchard with singer-songwriter Justin Lapoint’s blend of folk, bluegrass and blues.

    Free

  • Postpartum Circle with The Blooming Circle

    Nest and Gather 55 Deer View Lane, New Haven, VT

    Our regular third-Friday gathering. Come chat about motherhood and find connections with others.

    Free

  • Low Stimulation Library

    Bixby Memorial Free Library 258 Main Street, Vergennes, VT

    The third Saturday of every month, the library will open one hour early to allow for youth who need an ASD/sensory friendly environment to experience the library without excess stimulation. A calm, self-directed craft will also be provided.

  • Frost Mountain Nordic Ski Swap

    Mary Hogan Elementary School 201 Mary Hogan Dr., Middlebury, VT, United States

    Frost Mountain Nordic is hosting a ski swap event at Mary Hogan School, featuring Las Hermosas tacos and Cool Motion Outdoor Sports! Join us for some great deals on ski gear and eat some delicious tacos. The first 50 shoppers get a FREE pair of Darn Tough Socks! Ski swap equipment and apparel can be […]

    Free

  • Kids Cafe at the Marquis

    Middlebury Marquis Theatre 65 Main Street, Middlebury, VT, United States

    Settle in for a free family movie starting at 12:30pm at the Middlebury Marquis! This week's showing will be Sleeping Beauty.

    Free

  • Otter Creek Trunk Sale

    Otter Creek Child Center 150 Weybridge Street, Middlebury, VT, United States

    Clear out your closets, playrooms, and bookshelves for a great cause! We are excited to announce the Otter Creek Trunk Sale on Sunday, October 18, from 9:00 AM – 11:00 AM. This is a parking-lot style fundraiser where families sell gently used toys, baby gear, kids' clothes, and books directly from the trunk of their […]