From festive runs and family farms to vineyards and live music, here’s your local guide to celebrating Thanksgiving and the holiday season across Fairfield County.

🦃 Family Fun & Local Traditions

Thanksgiving Turkey Trots Across Fairfield County

Start your holiday on the right foot with a local turkey trot! These community runs combine fitness, fun, and festive spirit:

• Pequot Runners Thanksgiving Day 5-Mile Race — Nov 27 | Southport
  A beloved tradition along the coast and one of Connecticut’s oldest races.

• Stratford Turkey Day Trot — Nov 27 | Stratford, 8:15 AM
  A family-friendly run through Paradise Green.

• Ridgefield Turkey Trot (5K & Kids’ Fun Run) — Nov 27 | Ballard Park
  Supporting local charities and bringing the community together.

• Darien YMCA Turkey Trot — Nov 23 | Darien
  Scenic 5K and 1.5-mile routes perfect for all ages.

• Newtown Turkey Trot — Nov 28 | Fairfield Hills Campus
  A fun, family-oriented race with a great cause.

Local Markets & Seasonal Kickoffs

Holiday shopping feels more magical when you shop local:

• Glow Wild Lantern Festival — Through January | Connecticut’s Beardsley Zoo, Bridgeport
  35+ glowing lantern displays light up the night sky.

• CraftWestport — Nov 8–9 | Staples High School, Westport
  A juried fine crafts show — perfect for one-of-a-kind holiday gifts.

• Easton Winter Farmers Market — Saturdays through mid-November | Easton Firehouse
  Fresh pies, produce, and local goods for Thanksgiving tables.

• Fairfield Holiday Market on the Green — Nov 30 | Downtown Fairfield
  Artisans, live music, and Santa’s arrival on the Town Green.

• Bridgeport PAL Christmas Village — Opens Nov 30
  A classic holiday tradition with festive lights and family cheer.

• Wilton Holiday Stroll — Dec 6 | Wilton Center
  Carolers, local shops, and twinkling lights to kick off the season.

🌾 Farm & Family Adventures

Embrace small-town charm and outdoor fun this season:

• Jones Family Farms (Shelton) – Cut-your-own tree season begins right after Thanksgiving.

• Silverman’s Farm (Easton) – Holiday pies, cider, and festive decor.

• Boothe Memorial Park (Stratford) – Explore historic trails and buildings dressed for the holidays.

• Ambler Farm (Wilton) – Wreath-making workshops and cozy farmstand finds.

• Lachat Town Farm (Weston) – Seasonal markets and community events in a scenic setting.

🍂 Family Outings & Easy Escapes

• Stroll around Lake Mohegan (Fairfield) for the last of fall’s colors.

• Stop at Aspetuck Orchards (Easton) for fresh pies and cider to take home.

• Visit the Connecticut Air & Space Center (Stratford) for a hands-on look at local aviation history.

• Warm up at Firepit Fridays at The Adventure Park (Bridgeport) — ziplining, music, and cocoa under the stars.

💙 Give Back & Gather

Give thanks by giving back:

• Operation Hope Thanksgiving Food Drive — Fairfield | Donations accepted through mid-November.

• Wilton Social Services Holiday Basket Program — Help local families in need.

• Bridgeport Rescue Mission’s Great Thanksgiving Project — Volunteer or donate to support neighbors this holiday season.

🍷 Adult Escapes & Autumn Evenings

Vineyards & Tasting Nights

Relax, sip, and savor Connecticut’s wine country charm:

• Aquila’s Nest Vineyard (Newtown) – Fireside tastings and live music.

• Jones Winery (Shelton) – Barrel tastings and local bites.

• Gouveia Vineyards (Wallingford) – Mulled wine and panoramic hilltop views.

• Chamard Vineyards (Clinton) – Romantic setting with seasonal menus and music.

Arts, Music & Cozy Nights Out

Experience Fairfield County’s thriving arts scene:

• Fairfield Theatre Company (FTC) – Local and national live acts.

• Quick Center for the Arts (Fairfield University) – World-class performances and dance.

• SHU Community Theatre (Fairfield) – Movies, concerts, and holiday specials.

• Edgerton Center for the Performing Arts (SHU) – Theater and student showcases.

• Klein Memorial Auditorium (Bridgeport) – Symphony and Broadway performances.

• Bijou Theatre (Bridgeport) – Intimate comedy and live music shows.

• Ridgefield Playhouse (Ridgefield) – Concerts, films, and big-name entertainment.

Sports & Live Action

Cheer on the Bridgeport Islanders (AHL Hockey) at Total Mortgage Arena, Bridgeport’s waterfront stadium.

• Nov 2 – Springfield Thunderbirds | 3 PM

• Nov 5 – Lehigh Valley Phantoms | 7 PM

• Nov 8 – Springfield Thunderbirds | 7 PM

• Nov 12 – Wilkes-Barre/Scranton Penguins | 10:30 AM (School Day Game)

• Nov 15 – Rochester Americans | 7 PM

• Nov 28 – Springfield Thunderbirds | 3 PM

✨ Celebrate the Season Locally

Whether you’re running a 5K, picking out your Christmas tree, or discovering a new favorite vineyard, Fairfield County offers countless ways to celebrate the season close to home.
Embrace the holidays, support local, and make memories that remind you why Connecticut’s coastal and countryside towns shine this time of year.