Garlic Fest, Pumpkin Fun, Wine Trails, And Fairgrounds Light Up CT’s Oct. 10–12

CONNECTICUT — As October rolls along, Connecticut is serving up a long weekend full of flavor, fall fun, and community spirit. From garlic to grapes, pumpkins to kindness runs, this weekend (Oct. 10–12) is all about celebrating autumn’s best traditions. Whether you’re here for farm-fresh food, live music, or a little Halloween magic, there’s something happening in every corner of the state.

If there’s one event that truly captures the essence (and aroma) of fall, it’s the Connecticut Garlic & Harvest Festival at the Bethlehem Fairgrounds, happening Oct. 11–12. Garlic lovers can enjoy everything from garlic dips and spreads to garlic ice cream (yes, it’s a thing). Dozens of food vendors, crafters, and musicians round out the festival, while cooking demos and kids’ activities keep the whole family entertained. Don’t forget to grab a few bulbs to take home for your next pasta night.

The Riverton Fair (Oct. 10–12) is a picture-perfect Connecticut tradition set along the Farmington River. Celebrating more than a century of small-town charm, the fair features ox pulls, tractor contests, live music, a craft barn, and all the fair food you could dream of. From fried dough to pie-eating contests, it’s the ideal fall weekend for families—and for anyone who wants to soak up the season surrounded by foliage.

On Saturday, Oct. 11, the 21st Annual Prospect Pumpkin Festival lights up the town green with all things orange. Expect pumpkin carving, a pumpkin bake-off, contests, crafts, and live entertainment. It’s a wholesome, free community event that’s all about fall family fun—and yes, there’s plenty of pumpkin pie.

Raise a glass in downtown Milford on Saturday, Oct. 11, for the 16th Annual Downtown Milford Wine Trail. This self-guided tasting event pairs fine wines with local bites as visitors explore shops and restaurants throughout the downtown area. It’s part wine tasting, part walking tour, and all local flavor. Tickets include tastings at multiple locations and a souvenir glass.

If you’re looking to kick off spooky season early, head to the Mattatuck Museum in Waterbury for Family Fun Dayz: Halloween Spooktacular on Saturday, Oct. 11. Families can enjoy costume parades, arts and crafts, storytelling, and trick-or-treating through the museum. It’s the perfect balance of artsy and eerie.

Foodies will want to mark Sunday, Oct. 12, on their calendars for the Culinary Carnival at Stone Acres Farm in Stonington. Hosted by the Yellow Farmhouse Education Center, the event celebrates local food and sustainable farming with chef demos, tastings, and farm-fresh fare. There’s also live music, lawn games, and plenty of space to relax among the fields.

Running for a cause? The Race for Catherine – 5K for Kindness takes place Oct. 10–12 in Newtown. This family-friendly event encourages community connection and promotes acts of kindness, with proceeds supporting local charities. Whether you’re running, walking, or cheering from the sidelines, it’s a feel-good way to start your weekend.

With garlic in the air, pumpkins on parade, and wine glasses clinking, this October weekend in Connecticut is bursting with seasonal spirit. Whether you’re savoring slow food in Stonington, celebrating community in Prospect, or catching some live music under the fairground lights, it’s the perfect time to embrace autumn.