It’s the most spooktacular time of the year in Fairfield County! From pumpkin festivals and pup parades to glowing lanterns and Halloween fun, there’s no shortage of local magic happening across our towns. Whether you’re searching for a family outing, a costume event, or just a reason to enjoy crisp fall air, here’s your ultimate guide to the best Fairfield County fall and Halloween events this season.

🍁 Weekend of October 17–19

Fairfield

• Trunk or Treat at Elicit Brewing — Fri, Oct 18 | Elicit Brewing Co.
  Kick off the weekend with the MOMbies and a festive night of costumes, candy, and craft beer.

• Fairfield Harvest Market — Sat, Oct 18 | Downtown Fairfield
  Local vendors, food, music, and family fun on the Green.

• Dog Costume Parade on the Green — Sun, Oct 19, 12 PM | Fairfield Town Green
  A beloved annual tradition where furry friends show off their Halloween best.

Wilton

• Scarecrow Fest — Oct 15–31 | Wilton Center

• Wilton Pumpkin Festival — Sat, Oct 18, 12–4 PM | Wilton Historical Society

• Trick or Treat with the Horses — Sat–Sun, Oct 18–19 & Oct 25–26, 1–4 PM | Rising Starr Horse Rescue

• Family Halloween Spooktacular — Sat, Oct 18 | Wilton Riverbrook Regional YMCA

Westport

• Family Halloween Spooktacular — Sat, Oct 18, 3–5 PM | Westport Weston YMCA

• Murder Mystery Campfire — Sat, Oct 18 (Evening) | Earthplace

Darien

• Tokeneke Elementary Pumpkin Carnival — Sat, Oct 18

• Howl-O-Ween Pup Parade — Sun, Oct 19 | Downtown

Redding

• New Pond Farm Harvest Festival — Sat, Oct 18, 11 AM–4 PM | New Pond Farm

Milford

• Fall Artisan Market — Oct 18–19 | Milford Green

Bridgeport

• Foolproof Brewing Oktoberfest — Sat, Oct 18, 12–9 PM | Bridgeport

• Glow Wild Lantern Festival — Fri–Sun, Oct 17–19, 5–9 PM | Beardsley Zoo

Stamford

• Luckypawlooza — Sun, Oct 19 | Mill River Park

Trumbull

• Great Pumpkin Classic 5K — Sun, Oct 19 | Trumbull High School

Easton

• Falloween on the Farm — Sun, Oct 19 | Sport Hill Farm

Norwalk

• Artists of Norwalk House Tour — Sun, Oct 19, 12:30–4:30 PM | Norwalk Historic District

👻 Weekend of October 24–26

Fairfield

• Halloween Drive-In Movie — Thu, Oct 24, 6 PM | Lake Mohegan

• Haunted Candy House Workshop — Sat, Oct 25 | Fairfield Museum & History Center

• Halloween on the Green — Sun, Oct 26, 12–4 PM | Downtown

Wilton

• Trick or Treat with the Horses — Sat–Sun, Oct 25–26, 1–4 PM

• Wilton Pumpkin Parade — Sat, Oct 25

• Family Fun Halloween 5K — Sat, Oct 25

Milford

• Halloweekend on the Green — Oct 24–25

Greenwich

• Round Hill Volunteer Fire Co. Oktoberfest — Fri, Oct 24, 7–10 PM | Round Hill Community House

Norwalk

• Halloween Nightfair — Sat, Oct 25, 2–10 PM | Washington Street, SoNo

• Beasties & Besties Halloween Bash — Sat, Oct 25 | Stepping Stones Museum

New Canaan

• Touch-A-Truck — Sat, Oct 25 | Downtown

• Downtown Halloween Parade — Sun, Oct 26, 12–2 PM | Elm Street

Stamford

• Heckscher Farm Trick-or-Treat — Sun, Oct 26, 1–3 PM | Stamford Museum & Nature Center

• Stamford Town Center Candy Crawl — Sun, Oct 26 | Stamford Town Center

• Halloween Party at Stamford Yacht Club — Sat, Oct 25

• The Halloween Bar Crawl — Sat, Oct 25 & Thu, Oct 31

Trumbull

• Annual Fall Festival — Sun, Oct 26, 10 AM–2 PM | Town Hall Green

Bridgeport

• Glow Wild Lantern Festival — Weekend of Oct 24–26 | Beardsley Zoo

🕸️ Halloween Week (Oct 29–31)

Westport

• Annual Halloween Parade — Wed, Oct 29, 3:30 PM | Downtown

Ridgefield

• Boo Ride — Thu, Oct 30, 7–8 PM | Ridgefield Bicycle Co.

• Halloween Cycle — Fri, Oct 31, 9:30 AM | Ridgefield Recreation Center

Norwalk

• Tricks & Treats Day — Thu, Oct 31 | Stepping Stones Museum

• Halloween at Stew Leonard’s — Thu, Oct 31

Stamford

• The Halloween Bar Crawl (Encore) — Thu, Oct 31 | Downtown

Bridgeport

• Glow Wild Lantern Festival — Through Oct 31 | Beardsley Zoo

🍂 Celebrate Local, Support Local

From pumpkin patches to parades, every corner of Fairfield County is alive with the spirit of fall. Whether you’re trick-or-treating with your little ones or enjoying a night of Oktoberfest fun, there’s something here for everyone.

📍 Your hometown neighbors at Fowler Sakey Team | Coldwell Banker Realty