As the holiday season settles into Fairfield County, our towns are glowing with festive markets, tree lightings, concerts, and family-friendly traditions. Every two weeks, we round up the best events happening from Greenwich to Westport—fresh ways to celebrate the season, support local organizations, and make memories close to home. Whether you’re looking for beloved annual traditions, creative shopping experiences, or magical moments with Santa, here are the top five things to do around town right now.
Across Fairfield County
- 17th Annual Greenwich Reindeer Festival & Santa’s Workshop
Nov 28 through Dec 24 at Sam Bridge Nursery & Greenhouses, 437 North St, Greenwich. Photo ops with Santa and live reindeer, family fun.
- Harbor Point 15th Annual Christmas Tree Lighting
Sat Dec 6, 4-7 pm at Commons Park, Harbor Point, Stamford. Celebrate the season with live music, hot cocoa, Santa photos, and the official lighting of the Christmas tree. - Rowayton Gardeners Christmas Market
Sat Dec 6, 9 am, Pinkney Park, 177 Rowayton Ave, Norwalk.
- Holiday Makers Market at Westport Library
Sat Dec 6, 10 am-4 pm, featuring local crafters and gifts. - Norwalk Symphony Holiday Pops Concert
Sun Dec 7, 3-5 pm, Norwalk (25 Van Zant St). Festive symphonic performance perfect for the season.
Greenwich
- 17th Annual Greenwich Reindeer Festival & Santa’s Workshop
Nov 28 through Dec 24 at Sam Bridge Nursery & Greenhouses, 437 North St, Greenwich. Photo ops with Santa and live reindeer, family fun. - 2025 Chamber Holiday Party
Tue Dec 9, 5:30-7:30 pm at Hyatt Greenwich, 1800 E Putnam Ave, Old Greenwich. Networking and holiday cheer for local businesses. - All-Members Winter Exhibition Reception
Mon Dec 8, 6-7:30 pm at Bruce Museum, Greenwich. Celebrate the new winter exhibitions.
- Holiday Boutique – Greenwich Historical Society
Wed Dec 3 (5:30-8 pm) & Thu Dec 4 (9:30-4:30 pm) at Greenwich Country Club, 19 Doubling Rd. Holiday shopping for a cause.
- Holiday Fun Fest
Sun Dec 7 at Round Hill Community Church, Greenwich. Family-friendly festivities with crafts and light bites.
Stamford
- Heights & Lights
Sun Dec 7, 5 pm downtown Stamford (One Landmark Square to Latham Park). Santa and friends rappel from the heights, followed by a tree lighting and fireworks.
- Harbor Point 15th Annual Christmas Tree Lighting Sat Dec 6, 4-7 pm at Commons Park, Harbor Point, Stamford. Celebrate the season with live music, hot cocoa, Santa photos, and the official lighting of the Christmas tree.
- Holiday Stroll at Mill River Park
Daily through Dec 24 with food vendors, music, and lights.
- Holiday Wish Express at Stamford Town Center
Open through Dec 28, step inside an immersive winter wonderland at Stamford Town Center, where families can enjoy dazzling lights, themed rooms, and a magical journey to the North Pole with Santa and Mrs Claus.
- The Maritime Aquarium at Norwalk
Discover fun for all ages at this seasonal extravaganza featuring Santa doing shark dives, snow-machine indoor flurries, and a special sensory-friendly evening on December 9. Different events continue through December.
New Canaan, Darien + Rowayton
- Rowayton Holiday Stroll
Fri Dec 5 (6-8:30 pm) & Sat Dec 6 (11:45 am-8:30 pm), Pinkney Park, Rowayton. Santa arrives by boat, live music, and a toy drive.
- Rowayton Gardeners Christmas Market
Sat Dec 6, 9 am, Pinkney Park, 177 Rowayton Ave, Norwalk.
- Film Screening: The Ice Storm
Mon Nov 24, 6-8 pm at New Canaan Library.
- Music at Grace Farms Dec 13
3:30-4:30 pm at Grace Farms, 365 Lukes Wood Rd. Broadway Inspirational Voices returns to Grace Farms with a site-responsive program that connects us with the presence of the human voice to inspire the audience toward joy.
- A Christmas Carol Screening
Fri Dec 12, 7 pm, United Church of Rowayton, 210 Rowayton Ave, Norwalk. This performance will benefit Shakespeare on the Sound.
Westport, Weston & Wilton
- Norwalk Symphony Holiday Pops Concert
Sun Dec 7, 3-5 pm, Norwalk (25 Van Zant St). Festive symphonic performance perfect for the season. - Downtown Westport Tree Lighting Celebration
Fri Dec 5, 5 pm, Westport Center. Community tree lighting, hot chocolate, and caroling.
- Holiday Makers Market at Westport Library
Sat Dec 6, 10 am-4 pm, featuring local crafters and gifts.
- Weston Holiday Music Festival and Tree Lighting
Thu Dec 4, Weston Town Green at Town Hall. Hot chocolate and treats will be provided. - Winter Solstice Nature Walk
Tue, Dec 2, 6-8pm and Thu, Dec 4, 6-8pm, Earthplace, Westport. A festive holiday wreath-making event using natural materials foraged from the sanctuary!