Turkey Trots, Holiday Markets, Tree Lightings & Family Fun Across Every Town

As the leaves settle and the holidays begin, Fairfield County comes alive with festive markets, community runs, town traditions, and family-friendly celebrations. Whether you're looking for a Thanksgiving 5K, a charming makers’ market, a tree-lighting ceremony, or a magical holiday stroll, November is packed with events across all towns.

Use this guide to plan your month and kick off the holiday season locally.

🦃 Turkey Trots & Fall Runs

Bethel

Bethel Turkey Trot (5K)
📍 Bethel Municipal Center
🗓️ Nov 27 | 8:00 am

Darien

Overstuffed Turkey Trot (5K & 1-Mile)
🗓️ Nov 28

Fairfield / Southport

Pequot Runners Thanksgiving Day Race (5-Mile & 2.6-M Walk)
📍 Southport
🗓️ Nov 27 | 8:15 am

Greenwich

Greenwich Alliance Turkey Trot (5K & 1-Mile)
📍 Arch Street Teen Center area
🗓️ Nov 29
⏰ Mini Trot 9:00 am; 1-Mile 9:30 am; 5K 10:00 am

New Canaan

New Canaan Turkey Trot (5K)
📍 Waveny Park (Main House)
🗓️ Nov 23 | 11:30 am

New Fairfield

Run for the Turkeys (5K & Walk)
📍 54 Gillotti Rd
🗓️ Nov 23 | 11:00 am

Newtown

Newtown Turkey Trot (5K & 2.5K Walk)
🗓️ Nov 27

Norwalk / Rowayton

Rowayton Turkey Trot (5K & 1-Mile)
📍 Rowayton Community Center
🗓️ Nov 27 | 9:00 am

Redding

Joyce Allen Great Turkey Escape (5K & Kids Run)
🗓️ Nov 27 | Morning

Ridgefield

Boys & Girls Club Turkey Trot (5K & Kids Fun Run)
🗓️ Nov 27 | 8:00–10:00 am

Shelton

Commodore Hull Thanksgiving Day 5K
📍 Downtown Shelton/Derby
🗓️ Nov 27

Stratford

Stratford Turkey Day Trot
📍 Main Street
🗓️ Nov 27 | 8:15 am

🎁 Holiday Markets, Bazaars & Gift Shows

Easton

Holiday Fair – Church on the Green
🗓️ Nov 15 | 9:00 am–3:00 pm

Fairfield

Holiday Pop-Up Market – Fairfield Museum & History Center
🗓️ Nov 14 (4–8 pm) & Nov 15 (10 am–4 pm)

Greenwich

Greenwich Reindeer Festival & Santa’s Workshop
📍 Sam Bridge Nursery
🗓️ Nov 28 – Dec 24 | 12–6 pm (closed Sundays)

New Canaan

Blossom Hill Holiday Bazaar – Carriage Barn Arts Center
🗓️ Nov 21 | 5:30 pm–9:00 pm

Newtown

Holiday Fair
📍 Church Green & Indoor Activities
🗓️ Nov 15 | 9:00 am–3:00 pm

Norwalk / Rowayton

Rowayton Arts Center Holiday Gift Show
🗓️ Opens late November & runs into December

Stamford

Union Memorial Church Holiday Fair
📍 58 Church St
🗓️ Nov 15 | 10:00 am–3:00 pm

Weston

Main Street Weston Holiday Market – Emmanuel Church
🗓️ Nov 15 | 10:00 am–3:00 pm

Wilton

2nd Annual Marché Holiday Market
📍 WEPCO Complex
🗓️ Nov 29 | 10:00 am–3:00 pm

✨ Tree Lightings, Festivals & Holiday Experiences

Bridgeport

Glow Wild Lantern Festival – Beardsley Zoo
🗓️ Thurs–Sun evenings through November (check schedule)

Fairfield

Winter Whimsy – Tree Lighting & Holiday Festivities
📍 Old Town Hall & Museum Commons
🗓️ Nov 29 | 4:15 pm–7:00 pm

Stamford

Stamford Thanksgiving Parade Spectacular (giant balloons)
📍 Downtown Stamford
🗓️ Nov 23 | 12:00 pm
⭐ Balloon Inflation Party: Nov 22 | 3:00–6:00 pm

Holiday Wish Express – Stamford Town Center
🗓️ Nov 22 – Dec 28 | 5th floor

The Holiday Stroll – Mill River Park
🗓️ Nov 24 – Dec 24

Wilton

Great Trains Holiday Show – Wilton Historical Society
🗓️ Opens Nov 29; runs Wed–Sun through mid-January

Plan Your November Around Fairfield County’s Best Local Traditions

Whether you’re lacing up for a Turkey Trot, shopping local artisans, or kicking off the holiday spirit with tree lightings and festive strolls, November in Fairfield County offers something for every family, every schedule, and every town.