Odeen’s at Oak Hills Kicks Off Valentine’s Week—Trivia, Live Music & Special Dining All February Long!

The Moonrise Cartel brings folk rock and Americana to Garcia's in Port Chester on January 9, 2027, with special guests Unruly Mane. Get tickets!

Let the holiday madness begin! Discover tree lightings, holiday concerts, festive markets, dazzling displays & more in and around Fairfield County!

From Newtown to Stamford, Milford and beyond, discover where to shop local, find unique gifts and celebrate the holiday season! The holiday season is officially arriving in Fairfield County, and with it comes one of our favorite traditions — holiday markets, Christmas craft fairs, festive shopping strolls and artisan pop-ups! Whether you're searching for handcrafted jewelry, one-of-a-kind gifts, holiday decorations, specialty foods or something special for everyone on your shopping list, Connecticut's local holiday markets offer plenty of opportunities to shop small while enjoying the magic of the season. From bustling indoor craft fairs to charming outdoor holiday villages, Fairfield County and surrounding communities are preparing for weeks of festive fun. Fairfield After Dark has rounded up some of the holiday markets and shopping events to put on your calendar for November and December 2026! November 2026 Holiday Markets November 7–8 | CraftWestport — Westport, CT Location: Staples High School, Westport Saturday: 10 AM–5 PM Sunday: 10 AM–4 PM Kick off your holiday shopping at CraftWestport, one of the region's established fine craft events. Browse the work of approximately 175 artists and makers offering handmade jewelry, ceramics, home accessories, wearable art and other distinctive gifts. It's an excellent destination for shoppers who appreciate creativity, craftsmanship and gifts you won't find in a typical department store. Admission applies. November 7 | Popshop Market on Milford Green – Milford, CT Location: Milford Green, 84 S. Broad Street Time: 10am – 4 pm Come discover new brands, shop your PopShop favorites and support an incredible community of independent businesses throughout Fairfield County. Shop small. Shop local. Discover something different. November 7 | Shelton Autumn Craft Festival — Shelton, CT Location: Hyatt House Hotel, 830 Bridgeport Avenue Time: 10 AM–4 PM Get a head start on your holiday shopping at this indoor arts and crafts festival. Discover handmade creations from local and regional vendors while exploring gift ideas for friends, family and coworkers. November 13 & 14 | Holiday Pop-Up Market at Fairfield Museum – Fairfield, CT Location: Fairfield Museum, 370 Beach Road Time: 4pm-7pm Celebrate the holiday season at the 12th Annual Holiday Pop-Up Market, a festive two-day shopping experience featuring local vendors, talented artists, and makers offering handcrafted treasures, original artwork, specialty products, and unique gifts in a charming museum setting. November 14 | A Very Gifty Christmas — Danbury, CT Location: Danbury PAL, 35 Hayestown Road Time: 10 AM–4 PM Looking for a fun day of holiday shopping? A Very Gifty Christmas brings a seasonal marketplace to Danbury, offering an opportunity to browse vendor merchandise and discover gifts while supporting small businesses. November 14 | Milford Elks Holiday Market — Milford, CT Location: Milford Elks Club, 124 New Haven Avenue Time: 10 AM–3 PM Head to Milford for a community holiday market featuring local vendors and seasonal shopping opportunities. It's a great excuse to enjoy a Saturday discovering gifts close to home. November 15 | POPSHOP MARKET at Westport Museum – Westport, CT Location: Westport Museum, 25 Avery Place Time: 10am – 4pm Come discover new brands, shop your PopShop favorites and support an incredible community of independent businesses throughout Fairfield County. November 21–22 | Danbury Elks Holiday Craft Fair — Danbury, CT Location: Danbury Elks Club, 36 Sugar Hollow Road Saturday and Sunday Spend part of your weekend browsing holiday gifts, handmade items and seasonal merchandise at this Danbury holiday craft fair. November 21 | St. Theresa School Craft Fair — Trumbull, CT Location: St. Theresa School, 55 Rosemond Terrace Time: 9 AM–3:30 PM Community craft fairs are part of what makes the holiday season special. Stop by this Trumbull event for a day of seasonal shopping and the opportunity to support local vendors. November 20 - 22 | Ann's Place Festival of Trees – Danbury, CT Location: The Summit at Danbury – 100 Reserve Road Time: Friday, November 20th, Noon-7pm Saturday, November 21st, 10am-5pm Sunday, November 22nd, 10am-5pm December 2026 Holiday Markets December 5 | Shelton Holiday Craft Festival — Shelton, CT Location: Hyatt House Hotel, 830 Bridgeport Avenue Time: 10 AM–4 PM Still checking names off your holiday gift list? This December craft festival offers another opportunity to shop for handmade merchandise and discover something different. December 6 | Newtown Holiday Festival — Newtown, CT Location: Historic Main Street and Edmond Town Hall Time: 11 AM–4 PM for the holiday market One of Newtown's beloved holiday traditions returns with a festive day of shopping, entertainment and community celebrations! Explore holiday market vendors along historic Main Street and inside Edmond Town Hall while enjoying the charm of Newtown during the Christmas season. The larger festival also features seasonal activities such as the Festival of Trees, house tours, trolley tours and performances. Some activities require tickets or a festival pass, while shopping at the indoor market is free. It's the perfect opportunity to shop local, spend time with family and friends and celebrate the season in one of Fairfield County's most picturesque communities. December 6 | Holiday Art Market — Danbury, CT Location: Danbury Fair Mall, 7 Backus Avenue Time: 11 AM–7 PM Add a little creativity to your Christmas shopping! The Holiday Art Market at Danbury Fair Mall offers an opportunity to discover artwork and artisan merchandise while enjoying the convenience of shopping at the mall. December 12 | Redding Artisan Holiday Fair — Redding, CT Location: John Read Middle School, 486 Redding Road Time: 10 AM–4 PM For shoppers who prefer handcrafted gifts over mass-produced merchandise, the Redding Artisan Holiday Fair is another event worth adding to the calendar. December 12–13 | Holiday Market at Mill River Park — Stamford, CT Location: Whittingham Discovery Center, Mill River Park Time: 11 AM–5 PM both days Celebrate the season in downtown Stamford with a holiday market at Mill River Park. The weekend offers holiday shopping in a festive setting, with scheduled appearances by Santa and Mrs. Claus from 1–4 PM. Make an afternoon of it by exploring downtown Stamford's restaurants and nearby shops. December 12–13 | Holiday Market at Plasko Farm — Trumbull, CT Location: Plasko Farm, 670 Daniels Farm Road Enjoy a seasonal shopping outing at Plasko Farm, where a holiday market brings vendors together for a festive December weekend. Worth the Drive: Holiday Markets Beyond Fairfield County November 6–8 | New England Christmas Festival — Mohegan Sun, Uncasville With more than 400 artisans and specialty vendors, the New England Christmas Festival is one of Connecticut's largest seasonal shopping destinations. Find handcrafted gifts, holiday decorations, specialty merchandise and plenty of inspiration for your Christmas shopping list. December 4–5 | Bethlehem Christmas Town Festival — Bethlehem, CT Experience the charm of a small-town Connecticut Christmas with Bethlehem's annual holiday celebration. This seasonal tradition transforms the community into a festive destination featuring holiday shopping and hometown Christmas spirit. Shop Small. Celebrate Local. Make Holiday Memories. There's something special about buying a gift directly from the person who created it. Whether it's a handmade ornament, locally produced food, a beautiful piece of jewelry or a unique work of art, holiday markets make gift-giving more personal. And when you shop at local markets, you're doing more than checking items off your Christmas list. You're supporting small businesses, independent artists, local organizations and the communities that make Fairfield County such a wonderful place to live. So grab your friends, plan a holiday shopping adventure, enjoy a seasonal treat and discover something special this Christmas! Looking for more holiday happenings? From Christmas markets and tree lightings to holiday concerts, festive dining, live music and seasonal celebrations, Fairfield After Dark is your destination for discovering things to do throughout Fairfield County and beyond. Visit FairfieldAfterDark.com for more events, entertainment and holiday happenings! Event dates, hours, admission and vendor participation are subject to change. Please confirm details with organizers before attending

Milford, CT: Kick off the holiday shopping season with Popshop Market on Saturday, November 7, from 10 AM–4 PM on the historic Milford Green! Founded in 2012, Popshop Market is known for bringing together a thoughtfully curated mix of independent boutiques, emerging designers, artists, and small businesses for an elevated shopping experience. Discover an incredible selection of women’s apparel, jewelry, accessories, home decor, apothecary, vintage finds, specialty gifts, and one-of-a-kind treasures. Whether you’re checking names off your holiday shopping list or treating yourself to something special, there’s something for everyone to discover. More than just a market, Popshop is about celebrating creativity, discovering unique brands, and supporting the small businesses behind them. Follow @popshopmarket on Instagram for vendor spotlights, sneak peeks of what you’ll find, and updates on our upcoming holiday markets throughout Fairfield and New Haven Counties. Saturday, November 7 | 10 AM–4 PM Historic Milford Green | Downtown Milford, CT

Newtown, CT: Discover weekly happenings at Aquila's Nest Vineyards! Close out Halloween 2026 with costume parties, wine pairings, creative workshops and more.