May 2026 Event Calendar
May is one of the best months to get out and enjoy Fairfield County. From spring festivals and shopping events to local fairs, concerts, and community gatherings, there is something happening across the county all month long.
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MAY 1 TO MAY 3 |
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Friday, May 1 |
CT Foodie Fest | Milford Green | Milford Food trucks, local vendors, and a fun spring event on the Milford Green. |
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Friday, May 1 |
Home Sweet Home Spring Flower Show | Fairfield University Bookstore | Fairfield A seasonal flower show with spring inspiration in Fairfield. |
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Saturday, May 2 |
Community Cultural Celebration | Riverbrook YMCA | Wilton A family friendly community celebration with activities and local programming. |
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Saturday, May 2 |
NorWALK Mental Health Walk & Wellness Fair | Town Green | Norwalk A meaningful wellness event focused on connection and mental health awareness. |
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Saturday, May 2 |
Fairy House Festival | Greenwich YMCA | Greenwich A fun and creative spring event for families and children. |
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Saturday, May 2 |
Frog Frolic Festival | Redding A longtime local favorite with crafts, games, children’s activities, and music. |
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Saturday, May 2 to Monday, May 4 |
Minks to Sinks Tag Sale | Wilton A popular Wilton tradition with town wide tag sales and local finds. |
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Saturday, May 2 to Sunday, May 3 |
Miller Driscoll School Carnival | Wilton Classic carnival rides, games, food, and family fun. |
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Sunday, May 3 |
Breast Cancer Alliance 5K for Hope | Greenwich A community event supporting breast cancer awareness and research. |
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Sunday, May 3 |
EcoFest at Lachat Town Farm | Weston A spring event with music, family activities, vendors, and sustainability focused programming. |
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MAY 4 TO MAY 10 |
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Monday, May 4 |
Monday Morning Coloring Club | Darien Library | Darien A relaxed community event at Darien Library. |
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Tuesday, May 5 |
Mother’s Day Pop Up Shop | Greenwich Historical Society | Greenwich A local shopping event with thoughtful gifts and spring finds. |
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Wednesday, May 6 |
Shop & Stroll Into Spring | Downtown Fairfield | Fairfield An evening of local shopping, dining, and spring promotions in downtown Fairfield. |
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Thursday, May 7 |
Art to the Avenue Opening Night | Greenwich Avenue | Greenwich A signature Greenwich event where local businesses become gallery spaces. |
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Friday, May 8 |
New Canaan May Fair Friday Night Lights | New Canaan A fun kickoff to May Fair weekend with rides, food, and community energy. |
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Friday, May 8 to Saturday, May 9 |
Wilton Garden Club Mother’s Day Plant Sale | Town Green | Wilton A favorite Wilton tradition for gardeners and plant lovers. |
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Saturday, May 9 |
One of Fairfield’s favorite spring traditions with vendors, flowers, food, and family friendly activities. |
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Saturday, May 9 |
New Canaan May Fair | St. Mark’s Episcopal Church | New Canaan A classic local fair with rides, food, games, and family fun. |
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Saturday, May 9 to Sunday, May 10 |
Sunset Bazaar | 50 Water Street | Norwalk A SoNo event with shopping, local makers, music, and food. |
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MAY 11 TO MAY 17 |
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Monday, May 11 |
Monday Night Movie Night | Darien Library | Darien A simple local outing for movie lovers. |
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Tuesday, May 12 |
Tech Help Tuesday | Darien Library | Darien A helpful community program offering tech support. |
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Wednesday, May 13 |
Spring Fête: Design & Lifestyle | Greenwich Historical Society | Greenwich A design and lifestyle focused spring event. |
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Thursday, May 14 |
World Fair Trade Day Mindful Market | Grace Farms | New Canaan A thoughtful market featuring local makers and fair trade inspired shopping. |
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Friday, May 15 |
Friends of the Library Big Spring Book Sale | Fairfield Public Library | Fairfield A community favorite for readers and book lovers. |
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Friday, May 15 |
Greek food, music, dancing, and festival fun in Stamford. |
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Saturday, May 16 |
Rowayton School Carnival | Norwalk A local family carnival with rides, food, and games. |
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Saturday, May 16 |
St. Philip Spring Carnival | Norwalk Another fun Norwalk carnival weekend for families. |
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Saturday, May 16 |
Fairfield Hills Music Festival | Newtown Live music, food trucks, and a full day outdoors. |
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Sunday, May 17 |
Westport Dog Festival | Winslow Park | Westport A fun community event for dog lovers and families. |
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Sunday, May 17 |
Boothe Memorial Park Antique & Classic Car Show | Stratford A longtime Stratford tradition with antique and classic cars. |
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Sunday, May 17 |
Touch A Truck | Greenwich Town Hall | Greenwich A family friendly event in Greenwich. |
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MAY 18 TO MAY 24 |
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Monday, May 18 |
Community Craft Night | Wilton Library | Wilton A relaxed creative night at Wilton Library. |
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Tuesday, May 19 |
Mental Health Awareness Play Day | Town Hall | Trumbull A community event with family friendly activities and wellness programming. |
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Wednesday, May 20 |
Park Storytime: Highland Farm | Darien A sweet outdoor storytime for families. |
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Thursday, May 21 to Sunday, May 24 |
Ethos Greek Fest Carnival | Church of the Annunciation | Stamford A weekend of carnival rides, Greek food, and family fun. |
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Friday, May 22 to Monday, May 25 |
Weston Memorial Day Fair | Weston One of Weston’s biggest community weekends with rides, food, games, and entertainment. |
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Friday, May 22 |
St. Dimitrie Greek Festival & Carnival | Danbury A lively spring festival with food and carnival fun. |
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Saturday, May 23 |
Westport Fine Arts Festival | Downtown Westport & Church Lane | Westport Art, shopping, and downtown Westport energy. |
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Saturday, May 23 |
Greenwich Town Party | Baldwin Park | Greenwich A major Greenwich community event featuring Dave Matthews & Tim Reynolds. |
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Sunday, May 24 |
Westport Fine Arts Festival | Downtown Westport & Church Lane | Westport The second day of this favorite Westport arts weekend. |
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MAY 25 TO MAY 31 |
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Monday, May 25 |
Memorial Day Parades & Events | Throughout Fairfield County Communities across Fairfield County gather for Memorial Day parades and ceremonies. |
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Monday, May 25 |
Weston Memorial Day 5K & Family Fun Run | Weston High School | Weston A local race and family event on Memorial Day. |
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Tuesday, May 26 |
Easton Memorial Day Parade | Center Road to Town Hall | Easton A local Memorial Day community tradition. |
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Wednesday, May 27 |
Evening Garden Stroll | Bartlett Arboretum | Stamford A peaceful spring evening in the gardens. |
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Thursday, May 28 |
Author Talk: Local History | New Canaan Library | New Canaan A local history event at New Canaan Library. |
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Friday, May 29 |
Community Yoga on the Green | Town Green | Fairfield Outdoor yoga and community connection in Fairfield. |
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Saturday, May 30 |
SoNo Market | Washington Street | South Norwalk A local market with vendors, food, music, and shopping. |
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Sunday, May 31 |
Sunday Farm Market | Town Center | New Canaan Fresh produce, flowers, baked goods, and local vendors. |
Explore Fairfield County This May
From Fairfield and Westport to Greenwich, Stamford, Wilton, Norwalk, New Canaan, Weston, Stratford, Milford, Newtown, and beyond, May is packed with reasons to get out and explore locally. At Fowler Sakey Team, we love sharing the events, places, and community traditions that make Fairfield County such a wonderful place to live.
Looking for more local guides, Fairfield County events, and seasonal favorites? Subscribe to the Fowler Sakey Team newsletter for monthly updates, community highlights, and local recommendations.