Your 2025 Guide to Fairfield County’s Best Holiday Markets & Pop-Ups

 
If you love the festive energy of the holiday season, Fairfield County is delivering in a big way this year. Holiday markets are popping up everywhere, offering artisanal gifts, handcrafted décor, specialty treats, art, music, and plenty of community spirit.  As your local real estate advisors who know and love this area, we’re sharing our handpicked list of the best markets happening across the county. 
 

Holiday Salon - The Gift of Art 

November 8–December 23 • Silvermine Galleries, New Canaan 

A beautifully curated art showcase featuring original works by regional artists. 

Blossom Hill Holiday Bazaar - New Canaan 

November 21 • Carriage Barn Arts Center, New Canaan

Festive evening shopping supporting displaced youth. 

Greenfield Hill Commons Holiday Pop-Up Market 

November 22 • 10 AM–1 PM • 75 Hillside Road, Fairfield 
A cheerful neighborhood pop-up with local merchants and seasonal vendors offering great gift ideas — and one of our favorites because it’s right here in Greenfield Hill. 

New Canaan Nature Center - Holiday Market 2025 

November 22 • New Canaan 

Jewelry, clothing, candles, and handcrafted gifts. 

Darien Nature Center Holiday Market 

November 22 • Darien 

Handcrafted gifts, treats, and kid-friendly activities. 

Friends’ Holiday Boutique - New Fairfield 

November 29 • New Fairfield Library 

Handmade items, books, and seasonal gifts. 

Greenwich Historical Society - Holiday Boutique 

December 3–4 • Greenwich Country Club 

Curated vendors, raffles, and live music. 

Stamford Museum & Nature Center - Annual Holiday Market 

December 4 • Stamford 

Candles, soaps, scrubs, jewelry, tea, and décor. 

Rowayton Gardeners Christmas Market 

December 6 • Pinckney Park, Norwalk 

Designer wreaths, centerpieces, gifts & Silent Auction. 

CraftWestport 

December 6–7 • Staples High School, Westport 

170+ artisan vendors, one of CT’s largest markets. 

Pop Shop Holiday Market at Ellicit Brewing 

December 7 • Fairfield 

Modern pop-up with elevated artisan vendors. 

Light the Lights - Danbury 

December 6 • Danbury CityCenter Green 

Tree lighting celebration + local vendors. 

Mill River Park Holiday Market 

December 20–21 • Stamford 

Festive, family-friendly, last-minute shopping. 

Brookfield Craft Center - Holiday Shopping Tradition 

Through December 31 • Brookfield 

150+ artisans offering pottery, textiles, woodwork, and more. 

We hope this guide inspires you to get out, explore, and enjoy everything our community has to offer this season. If you spot us at a market, please say hi!