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!