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Local Guides
September 23, 2026

Oktoberfest & Fall Food Events in Fairfield County and Beyond (2026)

Oktoberfest & Fall Food Events in Fairfield County and Beyond (2026)

Beer tents, wine festivals and cider nights in a corn maze, from late September through Halloween

Oktoberfest season around here runs from late September to Halloween, and it isn't all beer tents. There are wine festivals, cider nights in a corn maze and farm parties with live music. Here's the lineup, in date order.

Late September

Sept. 23–Oct. 11: Oktoberfest at The Redding Roadhouse, Redding. Three weeks of Bavarian pretzels, schnitzel and sauerbraten, with German beers and local fall brews. An easy weeknight option if you can't make a weekend festival.

Opening weekend: Oct. 2–4

The first weekend in October is the busiest of the year. Pick one, or make a day of two.

  • Oct. 2: Twilight Brew Maze, Lyman Orchards, Middlefield. Craft beer tastings, corn maze admission and lawn games. Ages 21+.
  • Oct. 3: WineFest on Bedford, Latham Park, Stamford. Wines from around the world and live music in downtown Stamford, 3–5:30 p.m. Ages 21+.
  • Oct. 3: Westoberfest, Sigrid Schultz Plaza and Elm Street, Westport. More than 50 craft beers, live music, food vendors, local shopping and family activities. This is the one to bring the kids to.
  • Oct. 3: Darien Chamber Oktoberfest, The Gardener's Center, Darien. Live music, German-inspired food, beer, wine, cocktails, games and a silent auction. Ages 21+.
  • Oct. 3–4: Oktoberfest Finale, Half Full Brewery, Stamford. Seasonal beer releases, live music, beer-garden games, steinholding and Hammerschlagen.

Mid-October

  • Oct. 16: Twilight Hard Cider Maze, Lyman Orchards, Middlefield. Hard cider tastings, corn maze admission and lawn games. Ages 21+.
  • Oct. 18: The Beer Garden at the Farm, Wakeman Town Farm, Westport. Live music, food, farm animals, local vendors and activities for kids.

Late October

  • Oct. 24: Smoke in the Valley Craft Beer Festival, BADSONS Beer Co., Derby. Unlimited tastings, a home-brew competition, food trucks, vendors and live music. Ages 21+.
  • Oct. 31: Halloween Flashlight Brew Maze, Lyman Orchards, Middlefield. Craft beer tastings and the corn maze after dark, plus yard games. Ages 21+, and bring a flashlight.

Not a festival person?

Some of the best fall afternoons are the low-key ones. Try a seasonal pour at Two Roads in Stratford, Nod Hill in Ridgefield or Spacecat in Norwalk. Spend an afternoon at Aquila's Nest Vineyards in Newtown or Jones Winery in Shelton. Or make a cider-and-donut run to Beardsley's in Shelton, Silverman's in Easton or Blue Jay Orchards in Bethel.

Most 21+ events sell tickets in advance and some sell out, so book ahead for the Lyman maze nights especially.

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