October is the month Fairfield County shows off. The trees turn, the farm stands fill up, and there's something happening in almost every town every weekend. Whether you want a quiet hike, a night out or a full day with the kids, here's where to start.

Get outside while the leaves are turning

• Hike for peak foliage at Devil's Den in Weston, Lake Mohegan in Fairfield or Bennett's Pond in Ridgefield.
• Walk or bike the Norwalk River Valley Trail, or catch Long Island Sound views at Sherwood Island State Park in Westport.
• Paddle the Saugatuck River or Candlewood Lake on a calm, crisp morning.
• Zipline through the trees at The Adventure Park behind the Discovery Museum in Bridgeport.
• Climb indoors at Rock Climb Fairfield, a short walk from the Fairfield Metro station.
• Take a foliage drive through Easton, Redding and Wilton, with a stop at Weir Farm National Historical Park.
• Go farther afield on the Essex Steam Train or to the covered bridges in Cornwall and Kent.

Fall traditions

Apple picking, hayrides and corn mazes. Pick apples and pears at Silverman's Farm in Easton or Lyman Orchards in Middlefield, then take a hayride and get lost in the corn maze at Castle Hill Farm in Newtown or Plasko's Farm in Trumbull. Our apple picking and pumpkin patch guide has every farm we recommend, from the ones close to home to the ones worth the drive. Find all you need to know with our  Apple Picking & Pumpkin Patches Near Fairfield County guide.

Haunted houses and Halloween fun. For the brave, Legends of Fear in Shelton, Fright Haven in Stratford and Harvest Fair After Dark in Fairfield are all close to home. Not sure what's too scary for your kids? Our guide to Connecticut haunted houses by age sorts them from gentle to terrifying, and our town-by-town Halloween guide lists the parades, trunk-or-treats and pumpkin festivals in 13 towns.

Breweries and Oktoberfests. Oktoberfest season starts at The Redding Roadhouse (Sept. 23–Oct. 11), and Oct. 3 is the big day: Westoberfest in Westport, the Darien Chamber Oktoberfest, and the Oktoberfest Finale at Half Full Brewery in Stamford (Oct. 3–4). Our Oktoberfest and fall food events guide has the full lineup in date order, and between festivals, you can pick a taproom from our guide to Fairfield County breweries.

GLOW Wild. After dark, see more than 40 illuminated lantern displays at GLOW Wild at Connecticut's Beardsley Zoo in Bridgeport, Thursdays through Sundays starting Oct. 1.

Arts, culture and live performances

• Museums: new exhibitions at the Bruce Museum in Greenwich, The Aldrich Contemporary Art Museum in Ridgefield and MoCA CT in Westport.
• Live music and shows: The Warehouse at Fairfield Theatre Company, the SHU Community Theatre in downtown Fairfield, Westport Country Playhouse and ACT of CT in Ridgefield.
• A classic night out: catch a double feature at the Mansfield Drive-In.

Oktober is for Beer, food and cheer!

Visit one of the local oktoberfests, food and drink festivals, a local brewery or explore one of the 125 breweries in CT along the beer trail! 

• Oktoberfest & Fall Food Events in Fairfield County and Beyond

• Fairfield County's Craft Beer Scene: Must-Visit Breweries

Make a day of it

• Stroll a downtown. Ridgefield, New Canaan, Westport and Fairfield all have independent shops, galleries and seasonal menus worth a slow afternoon.
• Newtown loop: a foliage drive, Castle Hill Farm, Aquila's Nest Vineyards and a walk around the Fairfield Hills campus.
• Nature day: Woodcock Nature Center in Wilton or Earthplace in Westport.
• City day: take Metro-North into New York for a museum, a matinee or a fall walk through Central Park.

Warm up with a local coffee

Start the day at Lorca in Stamford for churros and a cortado, or Zumbach's Gourmet Coffee in New Canaan, which has been roasting its own beans since 1992.

Event dates and times can change, so check with the organizer before you head out.

Get in the Halloween Spirit!

• Haunted Houses in Connecticut: What's Right for Your Kids
• Halloween 2026 in Fairfield County, Town by Town

On the calendar this October

• Oct. 2–4: Friends of the Easton Library Annual Book Sale, Easton Public Library
• Oct. 3: Stratford Apple Festival & Vendor Fair, Lordship Community Church
• Oct. 3: Jazz'n Downtown, Downtown Milford
• Oct. 3: Trumbull Dog Day Festival, Trumbull Town Hall Green
• Oct. 3–4: Family Fun Carnival, St. Francis of Assisi, Weston
• Oct. 4: World Animal Day, Connecticut's Beardsley Zoo, Bridgeport
• Oct. 4: Shelton Day, Veterans Memorial Park and the Riverwalk, Shelton
• Oct. 6: An Afternoon with Author Jane Green, Darien Library
• Oct. 8: An Evening with Bestselling Author Amor Towles, The Westport Library
• Oct. 10: Fall for Darien, Highland Farm, Darien
• Oct. 11: New England Guitar Society, Firehouse Gallery, Milford
• Oct. 17: 👉 Fairfield Harvest Market, Old Town Hall Green, Fairfield.  
  •  🎃 Stop by our table for fun actiities for the family! We can't wait to meet you! 
• Oct. 17: Great Wilton Pumpkin Fest, Wilton Historical Society
• Oct. 18: Broadway & Beyond with the New Haven Symphony Orchestra, Shelton Intermediate School
• Oct. 18: Great Pumpkin Classic, Trumbull High School
• Oct. 22: Forty Ways to Know a Tree with Biologist Joan Maloof, The Westport Library
• Oct. 24: Birding at the Bruce with Greenwich Audubon, Bruce Museum
• Oct. 26: Celebrating Harry Houdini and the History of Magic, The Westport Library
• Oct. 28: Wednesday Walks: Walk Around Fairfield, Fairfield Public Library
• Oct. 31: Abilis Choir, Cohen Abilis Advancement Center, Stamford

For families, the libraries have plenty more, from storytimes to movie matinees. Check each library's calendar for the full lineup.

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