A festive roundup of seasonal markets, craft fairs, and boutique pop-ups where local artisans bring holiday magic, this guide maps out every merry stop for your holiday shopping adventures
Blossom Hill Foundation Bazaar
November 21
Have a winter ball at Blossom Hill’s annual holiday bazaar, a community favorite featuring artisan gifts and proceeds that support meaningful local initiatives.
Location: Carriage Barn Arts Center, Darien
Website: blossomhill-foundation.org/bazaar
Darien Nature Center Holiday Market
November 22
Celebrate the season surrounded by nature. This one-day market features a curated selection of gifts, handmade crafts and festive treats in a scenic setting.
Location: Darien Nature Center, Darien
Website: dariennaturecenter.org/2025-holiday-market
New Canaan Nature Center Holiday Market
November 22
Kick off the holiday season with live music from School of Rock and over a dozen vendors selling jewelry, candles, apparel and gifts.
Location: 144 Oenoke Ridge, New Canaan
Website: newcanaannature.org
Terrain Cafe Holiday Market
November 22
Enjoy the festive season inside Westport’s own winter terrarium with treats, giftable greenery and local vendors at Terrain’s annual open house.
Location: 561 Post Rd. E., Westport
Website: events.shopterrain.com
Marché Holiday Artisan Market
November 29
A unique shopping experience in Wilton blending the work of local artisans, makers and growers. Free to attend, ideal for Small-Business Saturday shopping.
Location: Marché, 48 New Canaan Rd., Wilton
Website: marchewilton.com
Designs By Lee Small Business Saturday Holiday Market
November 29
Celebrate the season and support local small businesses at this festive market featuring handmade gifts, décor and holiday cheer. Shop for your Christmas tree, wreaths, roping and more while enjoying the lively garden-center atmosphere.
Location: 129 Interlaken Rd., Stamford
Website: designsbylee.com/events/small-business-saturday-holiday-market
Historic Rowayton Holiday Bazaar
November 29–30
The 13th annual event from 12 to 5 p.m. brings festive entertainment, a miniature train show and one-of-a-kind gifts to this charming coastal village.
Location: Pinkney Park, Rowayton
Website: historicrowayton.org/rhs-events
Santa Visits Fairfield
November 30
Fairfield Chamber of Commerce’s celebration takes place on Sherman Green and welcomes Santa at 10 a.m., festive holiday music and plenty of family fun. Enjoy a holiday market, horse and wagon rides ($5 per person) and a petting zoo, while local nonprofits spread cheer and community spirit.
Location: Sherman Green, Corner of Post Rd. & Reef Rd., Fairfield
Website: fairfieldctchamber.com
The Winter Market Greenwich Historical Society
December 1–3
A lively Greenwich tradition with 35-plus vendors offering jewelry, gifts, flowers and gourmet goods. Opening Night festivities on Dec. 1 include cocktails, music and early shopping access.
Location: Christ Church Greenwich, 254 E. Putnam Ave., Greenwich
Website: greenwichhistory.org
Carriage Barn Arts Center “Deck the Walls”
December 3
Art meets holiday spirit in this annual show of original, handcrafted works available for purchase.
Location: 681 South Ave., New Canaan
Website: carriagebarn.org
Stamford Museum and Nature Center Annual Holiday Market
December 4
Shop candles, jewelry and baked goods in the Bendel Mansion from 4 to 8 p.m.—a cozy, artisan-made market in a historic setting.
Location: 39 Scofieldtown Rd., Stamford
Website: stamfordmuseum.org
Darien Community Association’s Merry Meadowlands
December 5
The DCA’s annual market transforms its historic Meadowlands estate into a winter wonderland filled with handcrafted gifts, greenery and seasonal décor.
Location: 274 Middlesex Rd., Darien
Website: dariendca.org
Rowayton Arts Center Holiday Gift Show
December 5–24
A multi-week showcase of handcrafted works by local artists, perfect for browsing meaningful gifts all December long.
Location: 145 Rowayton Ave., Rowayton
Website: rowaytonarts.org
Designs By Lee Holiday Market & Photos with Santa
December 6
A family-friendly favorite featuring local vendors, festive décor and free photos with Santa (donations of new, unwrapped toys appreciated). While you’re there, shop for trees, wreaths, roping and gifts.
Location: 129 Interlaken Rd., Stamford
Website: designsbylee.com/events/holiday-market-photos-with-santa
Cookie Walk & Holiday Gift Market
December 6
Step into the spirit of the season at United Methodist Church’s beloved annual event. Shop a curated market of local vendors, holiday gifts and handmade crafts. Don’t miss the famous Cookie Walk—tables piled high with homemade cookies sold by the pound.
Location: United Methodist Church, 49 Weston Rd., Westport
Website: umcww.com
Rowayton Gardeners Christmas Market
December 6
A beloved annual tradition featuring fresh wreaths, local gifts and plenty of holiday cheer.
Location: 33 Highland Ave., Rowayton
Website: rowaytongardeners.org
5th Annual Westport Holiday Stroll
December 6
In partnership with Dan Woog’s 06880, this family-friendly event features live music, Santa photos, local deals and a festive market at Elm & Main.
Location: Downtown Westport
Website: westportdowntown.com/holiday-stroll
Mill River Park Holiday Market
December 21–22
A lively downtown destination with handcrafted gifts, live entertainment and food vendors—perfect for last-minute shopping.
Location: The Whittingham Discovery Center, 1040 Washington Blvd., Stamford
Website: millriverpark.org/holiday-market