The winter months are a great time to explore what’s happening close to home. From creative experiences and live performances to family friendly outings and community gatherings, this list highlights fun, meaningful ways to get out, support local organizations, and enjoy the towns we love.
Across Fairfield County
- 20th Annual BGCG Swim A Thon
Sunday, January 25, 2026
Boys and Girls Club of Greenwich, Greenwich
A community wide fundraising event supporting local youth programs, bringing together swimmers of all ages to support the Boys and Girls Club of Greenwich. - Super Splash 2026
Sunday, February 1, 2026
Cove Island Park, Stamford
An annual winter fundraising event where participants take part in a cold water splash to support a local nonprofit. - Learn to Play Mahjong
Wednesday, January 28, 2026
New Canaan YMCA, New Canaan
A four class beginner series introducing the basics of mahjong, including rules, strategy, and gameplay. Registration is for the full series, with additional class dates listed on the event page. - Wilton’s Winter Carnival, Fire and Ice
Sunday, February 1, 2026
Wilton Town Green, Wilton
A community winter celebration featuring fire and ice themed activities designed for families to enjoy together. - Lockwood Mathews Mansion Museum Self Guided Visit
Multiple dates between Friday, January 23, 2026 and Thursday, February 5, 2026
Lockwood-Mathews Mansion Museum, Norwalk
Explore one of Connecticut’s most significant historic homes during regular museum hours.
Greenwich Magazine
1. 20th Annual BGCG Swim A Thon
Sunday, January 25, 2026
Boys and Girls Club of Greenwich, Greenwich
A community wide fundraising event supporting local youth programs, bringing together swimmers of all ages to support the Boys and Girls Club of Greenwich.
2. Greenwich Symphony Orchestra January Concert Series
Saturday, January 24, 2026 and Sunday, January 25, 2026
Greenwich High School Performing Arts Center, Greenwich
The Greenwich Symphony Orchestra presents its January concert program featuring classical repertoire performed by professional musicians.
3. Greenwich Winter Farmers Market
Saturday, January 31, 2026
Sam Bridge Nursery & Greenhouses, Greenwich
An indoor winter market featuring local produce, baked goods, specialty foods, and artisan goods from regional vendors.
4. Family Floral Fun Series, Winter Forest Hike and Sustainable Art Experience
Saturday, February 1, 2026
Greenwich Historical Society, Greenwich
A hands on family program combining a guided winter forest hike with a sustainable art activity inspired by the natural landscape.
5. Houseplant Propagation Workshop, Plants From Plants
Thursday, February 5, 2026
Greenwich Botanical Center, Greenwich
Stamford Magazine
Super Splash 2026
Sunday, February 1, 2026
Cove Island Park, Stamford
An annual winter fundraising event where participants take part in a cold water splash to support a local nonprofit.
2. Improv Comedy Jam
Saturday, January 24, 2026
Ferguson Library, Harry Bennett Branch, Stamford
A live improv comedy program featuring spontaneous performances and audience participation, geared toward teens and adults.
3. Sunday Funday at Mill River Park
Sunday, January 25, 2026
Mill River Park, Whittingham Discovery Center, Stamford
A family program featuring a kids read along, free snacks, and an activity, with a different story featured each week.
4. Animals for All, Caring for Exotic Critters
Saturday, January 31, 2026
Stamford Museum and Nature Center, Stamford
A hands on educational program introducing participants to exotic animals and the care involved in working with unique species.
5. Super Diamond
Friday, January 30, 2026
The Palace Theatre, Stamford
A high energy tribute concert celebrating the music of Neil Diamond, presented live at The Palace Theatre.
New Canaan, Darien and Rowayton Magazine
1. Learn to Play Mahjong
Wednesday, January 28, 2026
New Canaan YMCA, New Canaan
A four class beginner series introducing the basics of mahjong, including rules, strategy, and gameplay. Registration is for the full series, with additional class dates listed on the event page.
2. Adopt a Tree Kickoff Event
Saturday, January 24, 2026
New Canaan Nature Center, New Canaan
Kick off maple syrup season with a family friendly outdoor experience where participants learn the process, choose and tap a maple tree, and begin a season long program.
3. Valentine’s Bottle Painting
Thursday, February 5, 2026
Carriage Barn Arts Center, New Canaan
A creative, hands on workshop where participants paint decorative bottles inspired by Valentine’s Day themes.
4. Lockwood Mathews Mansion Museum Self Guided Visit
Multiple dates between Friday, January 23, 2026 and Thursday, February 5, 2026
Lockwood-Mathews Mansion Museum, Norwalk
Explore one of Connecticut’s most significant historic homes during regular museum hours.
5. Winter Sowing Workshop Demo
Saturday, January 24, 2026
Darien Library, Darien
A hands on demonstration introducing the winter sowing method and how to start seeds outdoors during the colder months.
Westport, Weston and Wilton Magazine
1. Big Band Broadway
Thursday, January 29, 2026 through Sunday, February 1, 2026
Westport Country Playhouse, Westport
A high energy concert style salute to Broadway favorites, backed by big band sound and showstopping vocals.
2. Wilton’s Winter Carnival, Fire and Ice
Sunday, February 1, 2026
Wilton Town Green, Wilton
A community winter celebration featuring fire and ice themed activities designed for families to enjoy together.
3. Rock and Roll Playhouse, The Music of Chappell Roan and More for Kids
Saturday, January 31, 2026
Fairfield Theatre Company, The Warehouse, Fairfield
A live, family friendly concert introducing kids to popular music through interactive performances and movement.
4. Paint It
Saturday, January 31, 2026
Wilton Library, Wilton
A guided paint program where participants follow step by step instruction to create their own artwork.
5. WestportREADS Film Series, Waterworld
Wednesday, January 28, 2026
Westport Library, Westport
A screening of the film Waterworld as part of the WestportREADS film series.