Looking for things to do in Fairfield County this week and next, early May has a little more texture than the usual spring calendar. There are colorful festivals, pop up markets, author conversations, theater, music, and creative workshops that make a plan feel easy without needing to overthink it. The season shows up in the details, flowers for the garden, art in storefront windows, music on stage, and families gathering outdoors again. A few of these events invite you to make something or learn something, while others are simply a chance to listen, browse, laugh, or settle into a good story. It is a good reminder that the best weekends often start with what is happening right nearby.
Across Fairfield County
1. Art Walk, Art to the Avenue
Thursday, May 7, 2026
Greenwich Avenue, Greenwich
Greenwich Arts Council turns Greenwich Avenue and nearby streets into a strolling gallery, with local artwork displayed inside participating shops and businesses. Opening night brings visitors downtown to browse the work, meet artists, and move between storefronts at an easy pace. The art remains on view through May 25, giving the event a longer life beyond the first evening.
2. Film Screening, Encanto with Avon on Tour
Saturday, May 2, 2026
Stamford Town Center, Stamford
Avon on Tour presents a free screening of Encanto in collaboration with Stamford Moms. Families can arrive early for activities before the movie begins, then settle in for Disney’s story of the Madrigal family and Mirabel’s search for her own place in it. No tickets are needed, and seating is first come, first served.
3. Musical, Next to Normal
Saturday, May 2, 2026
New Canaan Library, New Canaan
CT Stage Co. presents a staged concert version of the Pulitzer Prize and Tony Award winning musical. The story follows a suburban family navigating mental illness, grief, and the fragile ways people try to hold one another together. The pop rock score by Tom Kitt and Brian Yorkey brings intensity and momentum to the staged concert format.
4. Festival, EcoFest at Lachat Farm
Sunday, May 3, 2026
Lachat Town Farm, Weston
EcoFest is a free family friendly celebration focused on sustainability, nature, and local environmental action. The day includes live student performances, food, hands on activities, local vendors, eco talks, animal programs, and children’s games and crafts. Families can also bring redeemable bottles and cans for a raffle or donate children’s books through the event’s book drive.
5. Concert, Andrew Duhon
Thursday, May 14, 2026
Fairfield Theatre Company, Fairfield
Andrew Duhon brings his New Orleans rooted songwriting to StageOne with a trio built around guitar, bass, drums, and strong storytelling. His music blends folk, country, blues, and Americana, with songs shaped by travel, memory, and connection. The performance offers an intimate night of live music centered on thoughtful lyrics and warm, roots based sound.
Greenwich Magazine
1. Garden Market, May Gardeners Market
Saturday, May 2, 2026
Greenwich Botanical Center, Cos Cob
Gardeners can browse seasonal plants, hear short talks, and spend time outdoors at this annual spring market. The day includes food vendors, educational sessions, and a family nature walk through the Montgomery Pinetum. Visitors can pick up ideas for home gardens while seeing what is coming into bloom at the center.
2. Festival, Community HoliFest 2026
Saturday, May 2, 2026
Roger Sherman Baldwin Park, Greenwich
The India Cultural Center brings HoliFest back to Greenwich with a full afternoon of color, music, dance, and food. The celebration includes performances, dance workshops, cricket batting cages, badminton courts, henna artists, a DJ, and a YMCA kids zone. The color throw gives the day its big shared moment, while the mix of activities makes it easy for families and groups to take part.
3. Music Lecture, Celebrating American Voices
Wednesday, May 6, 2026
Greenwich Library, Greenwich
Musicologist Gil Harel leads a Peterson Music lecture celebrating America’s 250th through the work of three composers. The program looks at how American energy, identity, and sound come through in music. Listeners can connect the music to larger questions of American identity and artistic voice.
4. Family Program, Sew Much Fun
Sunday, May 10, 2026
Greenwich Historical Society, Cos Cob
Families and visitors can explore how embroidery has decorated clothing and homes throughout history. The program connects the current Fashioning America exhibition with tours of Bush Holley House and a hands on stitching activity. Participants can learn simple stitches and create a historically inspired sampler to take home.
5. Art Walk, Art to the Avenue
Thursday, May 7, 2026
Greenwich Avenue, Greenwich
Greenwich Arts Council turns Greenwich Avenue and nearby streets into a strolling gallery, with local artwork displayed inside participating shops and businesses. Opening night brings visitors downtown to browse the work, meet artists, and move between storefronts at an easy pace. The art remains on view through May 25, giving the event a longer life beyond the first evening.
Stamford Magazine
1. Play, My Mother and the Michigan Ohio War
Friday, May 1, 2026
The Dressing Room Theatre, Stamford
A new comedy by Paul Stroili brings a family story into the orbit of the historic Michigan Ohio War. The play follows a family dealing with the death of its patriarch, whose obsession with the Toledo War left behind more than a few complications. The May 10 performance also includes a talk with the playwright.
2. Film Screening, Encanto with Avon on Tour
Saturday, May 2, 2026
Stamford Town Center, Stamford
Avon on Tour presents a free screening of Encanto in collaboration with Stamford Moms. Families can arrive early for activities before the movie begins, then settle in for Disney’s story of the Madrigal family and Mirabel’s search for her own place in it. No tickets are needed, and seating is first come, first served.
3. Guided Walk, Jane’s Walk Stamford
Saturday, May 2, 2026
Emerson Hall at Unitarian Universalist Congregation of Stamford, Stamford
The free community led walk explores downtown public spaces, local history, and the way people gather in the city. Architectural historian Wes Haynes and Stamford Downtown Special Services District President Michael Moore guide the walk from Emerson Hall south along Bedford Street. The event is open to all ages and designed around conversation, observation, and shared discovery.
4. Dance Performance, Shen Yun
Thursday, May 7, 2026
Stamford Palace Theatre, Stamford
Classical Chinese dance, live orchestral music, elaborate costumes, and animated backdrops come together in a large scale stage production. The performance draws on legends, ethnic traditions, and stories from thousands of years of Chinese culture. The production pairs spectacle with narrative scenes drawn from different cultural traditions.
5. Reception, Tiny Art Show Opening
Wednesday, May 6, 2026
Ferguson Library, Stamford
The Tiny Art Show opening celebrates the artists who created small scale works for the 2026 exhibition. The reception is open to all ages and brings together art, snacks, and a casual first look at the pieces. Visitors can see how much personality fits into a small canvas.
New Canaan, Darien and Rowayton Magazine
1. Musical, Next to Normal
Saturday, May 2, 2026
New Canaan Library, New Canaan
CT Stage Co. presents a staged concert version of the Pulitzer Prize and Tony Award winning musical. The story follows a suburban family navigating mental illness, grief, and the fragile ways people try to hold one another together. The pop rock score by Tom Kitt and Brian Yorkey brings intensity and momentum to the staged concert format.
2. Market, Rowayton Gardeners Spring Market
Saturday, May 9, 2026
Potting Shed, Rowayton
The annual spring market brings together locally sourced perennials, tomato plants, herbs, dahlias, hanging baskets, and fresh dahlia bouquets. Shoppers can also browse garden goods, vintage treasures, breads, pies, and cakes. Master Gardeners and arborists will be available to answer plant and yard questions.
3. Concert, Yacht Lobsters
Saturday, May 2, 2026
District Music Hall, Norwalk
Yacht Lobsters bring their yacht rock sound to a standing room concert at District Music Hall. The show leans into soft rock, retro grooves, and the breezy energy of 1970s and early 1980s favorites. The set moves through upbeat nostalgia, harmonies, and songs built for a night out.
4. Market, Mindful Market at Grace Farms
Thursday, May 7, 2026, through Sunday, May 10, 2026
Grace Farms, New Canaan
Grace Farms marks World Fair Trade Day with a pop up market featuring ethically sourced goods, teas, coffees, and small bites. Visitors can browse products from skilled craftspeople and responsible brands while spending time in one of New Canaan’s most distinctive gathering spaces. The market is free with daily registration.
5. Family Fair, May Fair
Saturday, May 9, 2026
St. Mark’s Episcopal Church, New Canaan
May Fair returns with rides, food, a White Elephant sale, strawberry shortcake, face painting, live entertainment, and a family dog show. The long running event has a full day feel, with plenty for children and adults to do without needing a complicated plan. The day moves between classic fair traditions and easy activities for children and adults.
Westport, Weston and Wilton Magazine
1. Market, PopShop Market
Saturday, May 2, 2026
Westport Museum for History and Culture, Westport
PopShop Market brings more than 30 vendors together for a spring shopping event with handmade clothing, gifts, accessories, and one of a kind finds. The market has an easy browse and linger feel, with plenty of options for Mother’s Day gifts, graduation presents, teacher gifts, or a small treat. Shoppers can move through the museum grounds while picking up seasonal goods and locally made finds.
2. Festival, EcoFest at Lachat Farm
Sunday, May 3, 2026
Lachat Town Farm, Weston
EcoFest is a free family friendly celebration focused on sustainability, nature, and local environmental action. The day includes live student performances, food, hands on activities, local vendors, eco talks, animal programs, and children’s games and crafts. Families can also bring redeemable bottles and cans for a raffle or donate children’s books through the event’s book drive.
3. Author Talk, LeUyen Pham
Saturday, May 9, 2026
Wilton Library, Wilton
Book fans can hear from LeUyen Pham, an award winning illustrator and author behind more than 140 children’s books. The conversation traces her creative path from animation to picture books, graphic memoirs, and beloved series like The Princess in Black. A book signing follows the presentation, with Elm Street Books on site.
4. Workshop, Westport Writers at MoCA CT
Thursday, May 14, 2026
MoCA CT, Westport
Writers of all levels can take part in an evening of writing inspired by the current exhibition Art, Jazz and the Blues. Amanda Parrish Morgan and Liz Matthews lead participants through observation based prompts, individual writing, collaborative exercises, and supportive sharing. The workshop connects visual art and language in a relaxed gallery setting.
5. Concert, Andrew Duhon
Thursday, May 14, 2026
Fairfield Theatre Company, Fairfield
Andrew Duhon brings his New Orleans rooted songwriting to StageOne with a trio built around guitar, bass, drums, and strong storytelling. His music blends folk, country, blues, and Americana, with songs shaped by travel, memory, and connection. The performance offers an intimate night of live music centered on thoughtful lyrics and warm, roots based sound.