Looking for things to do in Fairfield County this week and next. Mid June brings local events that make it easy to step out close to home, from outdoor concerts and summer fairs to garden workshops, book talks, and family programs. It is the kind of stretch when a farmers market, a museum visit, or a night of live music can turn an ordinary day into something more memorable. Across the county, familiar gathering places are filling up with warm weather energy and reasons to reconnect. Some plans feel relaxed and casual, while others offer a chance to learn something new or settle in for a performance. However you like to spend these longer days, there is plenty happening nearby that feels worth leaving the house for.
Across Fairfield County
1. Concert, Greenwich Jazz Festival Opening Night
Thursday, June 25, 2026
Round Hill Community House, Greenwich
BackCountry Jazz opens the Greenwich Jazz Festival with an evening built around cocktails, dinner, and live jazz. The event supports the organization’s summer artistic and education programming, including its free music camp for Bridgeport youth. Guests can expect a polished night of music in a warm community setting.
2. Festival, Stamford Summer Block Party
Saturday, June 20, 2026, and Sunday, June 21, 2026
Stamford Town Center, Stamford
The annual Summer Block Party returns with live entertainment, food, shopping, local vendors, and family activities. Children can enjoy face painting, balloon artists, games, and performances while adults browse the marketplace and sample food from the restaurant plaza. The weekend has an easy summer energy, with plenty to do for families, friends, and neighbors meeting up downtown.
3. Car Show, Caffeine and Carburetors
Sunday, June 14, 2026
Downtown New Canaan, New Canaan
Classic, vintage, and specialty cars fill downtown New Canaan for one of the area’s favorite warm weather gatherings. Visitors can walk through the displays, talk with car owners, and enjoy the easy energy of a summer morning in town. The event draws serious car enthusiasts and casual browsers alike, with plenty to see even for families stopping by for a short visit.
4. Author Panel, Ladies of Summer
Thursday, June 25, 2026
Wee Burn Country Club, Darien
Barrett Bookstore’s summer author event brings Kimberly McCreight, Hannah McKinnon, and Emma Straub together for a lively conversation about their newest books. The evening includes refreshments, an author panel, audience questions, and a signing. Readers can make it a social night out while adding a few new titles to their summer list.
5. Festival, Yankee Doodle Fair
Thursday, June 18, 2026, through Sunday, June 21, 2026
Westport Woman’s Club, Westport
The Westport Woman’s Club turns its grounds into a classic summer fair with carnival rides, games, food, raffles, and live entertainment. Families can make it a quick outing or stay longer for the rides and fair food. The event has the easy, familiar feel of a local tradition that works for kids, parents, and grandparents.
Greenwich Magazine
1. Family Program, Flag Day Fun
Sunday, June 14, 2026
Greenwich Historical Society, Cos Cob
Families can spend the day exploring Greenwich history through hands on activities, house tours, and special Flag Day programs. Visitors can see the unveiling of a newly restored 13 star flag, walk through the gardens, and learn how the American Revolution shaped the lives of the Bush household. In the classroom, children can learn about the historic tall ship Oosterschelde and make a miniature ship to take home.
2. Family Music, Silver Steel Drum Band
Thursday, June 25, 2026
Byram Shubert Library, Greenwich
Silver Steel Drum Band brings Soca and Calypso music to an outdoor family concert at Byram Shubert Library. The performance has an easy summer feel, with music rooted in the sounds of Trinidad and Tobago. It works well for families, adults, and anyone looking for a relaxed evening with live music.
3. Workshop, All Things Peonies
Thursday, June 18, 2026
Greenwich Botanical Center, Cos Cob
Floral designer Dijana Xocoy leads an evening workshop focused on the color, shape, and movement of peak season peonies. Participants will learn arranging techniques, including sustainable mechanics that use chicken wire instead of floral foam. The class blends demonstration with hands on design, ending with a finished peony arrangement to take home.
4. Environmental Event, Experience the Sound
Sunday, June 21, 2026
Greenwich Point Park, Old Greenwich
The Town of Greenwich Shellfish Commission hosts a hands on celebration of the shoreline, watersheds, and Long Island Sound. Visitors can explore demonstrations, exhibits, and activities connected to the coastal environment. The afternoon is free and family friendly, with plenty for children and adults to learn by seeing, touching, and asking questions.
5. Concert, Greenwich Jazz Festival Opening Night
Thursday, June 25, 2026
Round Hill Community House, Greenwich
BackCountry Jazz opens the Greenwich Jazz Festival with an evening built around cocktails, dinner, and live jazz. The event supports the organization’s summer artistic and education programming, including its free music camp for Bridgeport youth. Guests can expect a polished night of music in a warm community setting.
Stamford Magazine
1. Book Sale, Friends Book Shop Bag Sale
Saturday, June 13, 2026
Ferguson Library, Stamford
Readers can fill a bag with used books from the Friends Book Shop, with categories ranging from fiction and biographies to cookbooks, travel, sports, and children’s books. The sale is tied to the Arts & Crafts on Bedford street fair, so visitors can browse handmade goods nearby and leave with a stack of summer reading. Proceeds benefit library programs and services.
2. Ballet, Connecticut Ballet’s Giselle
Saturday, June 13, 2026
Stamford Palace Theatre, Stamford
Connecticut Ballet brings one of the great romantic ballets to the stage, with the story of a young woman betrayed by love and drawn into the supernatural world of the Wilis. The production features guest stars Oksana Maslova and Sterling Baca of Philadelphia Ballet as Giselle and Albrecht. With its mix of dramatic storytelling, classical dancing, and haunting atmosphere, the performance has an elegant evening out feel.
3. Exhibition, Printmaking and Unconventional Pathways
Friday, June 12, 2026, through Sunday, September 6, 2026
Stamford Museum & Nature Center, Stamford
A new exhibition explores African American artists who used printmaking as a creative practice, a collaborative medium, and a way to circulate art more widely. Curated by scholar and master printmaker Dr. Curlee Raven Holton, the show traces artists working beyond traditional pathways into the art world. Visitors can expect a thoughtful look at technique, history, resilience, and artistic voice.
4. Workshop, Planting for Pollinators
Monday, June 15, 2026
Bartlett Arboretum & Gardens, Stamford
This garden workshop focuses on how to create a thriving pollinator garden at home. Participants can learn practical ways to support bees, butterflies, and other beneficial pollinators through plant choices and habitat minded design. The program is a useful fit for gardeners who want their summer planting to feel both beautiful and purposeful.
5. Festival, Stamford Summer Block Party
Saturday, June 20, 2026, and Sunday, June 21, 2026
Stamford Town Center, Stamford
The annual Summer Block Party returns with live entertainment, food, shopping, local vendors, and family activities. Children can enjoy face painting, balloon artists, games, and performances while adults browse the marketplace and sample food from the restaurant plaza. The weekend has an easy summer energy, with plenty to do for families, friends, and neighbors meeting up downtown.
New Canaan, Darien and Rowayton Magazine
1. Car Show, Caffeine and Carburetors
Sunday, June 14, 2026
Downtown New Canaan, New Canaan
Classic, vintage, and specialty cars fill downtown New Canaan for one of the area’s favorite warm weather gatherings. Visitors can walk through the displays, talk with car owners, and enjoy the easy energy of a summer morning in town. The event draws serious car enthusiasts and casual browsers alike, with plenty to see even for families stopping by for a short visit.
2. Family Performance, Earth Songs
Saturday, June 13, 2026, and Sunday, June 14, 2026
Stepping Stones Museum for Children, Norwalk
Puppetry brings oceans, forests, skies, and animal habitats to life in a large scale show designed for young audiences. Children can follow giant puppets through different biomes while learning about ecology and the balance of the natural world. The performance is included with museum admission, making it easy to pair with a visit to the exhibits.
3. Historic Tour, Middlesex Parish Road Trip
The Mather Homestead, Darien
Darien’s historic sites open their doors for a Connecticut Open House Day program connected to America 250. Visitors can stop by the Mather Homestead for tours and explore local Revolutionary War history through the wider Middlesex Parish road trip. The afternoon offers a relaxed way to connect familiar places with the stories that shaped them.
4. Exhibition, Photography and Sculpture
Sunday, June 21, 2026, through Sunday, July 19, 2026
Rowayton Arts Center, Rowayton
Rowayton Arts Center presents an open juried show focused on photography and sculpture. The exhibition brings together work by artists exploring image, form, material, and perspective across two different mediums. Visitors can stop into the gallery for a fresh look at regional art in a welcoming neighborhood setting.
5. Author Panel, Ladies of Summer
Thursday, June 25, 2026
Wee Burn Country Club, Darien
Barrett Bookstore’s summer author event brings Kimberly McCreight, Hannah McKinnon, and Emma Straub together for a lively conversation about their newest books. The evening includes refreshments, an author panel, audience questions, and a signing. Readers can make it a social night out while adding a few new titles to their summer list.
Westport, Weston and Wilton Magazine
1. Festival, Yankee Doodle Fair
Thursday, June 18, 2026, through Sunday, June 21, 2026
Westport Woman’s Club, Westport
The Westport Woman’s Club turns its grounds into a classic summer fair with carnival rides, games, food, raffles, and live entertainment. Families can make it a quick outing or stay longer for the rides and fair food. The event has the easy, familiar feel of a local tradition that works for kids, parents, and grandparents.
2. Concert, Music in the Meadow
Saturday, June 13, 2026
Lachat Town Farm, Weston
Lachat Town Farm opens its summer concert series with indie rock band Morningside and a supporting set from Charlotte Roth. The evening brings live music to the farm, with food trucks and the barn bar available during the show. It is an outdoor concert setting with a relaxed start to the summer season.
3. Concert, Lucius at Levitt Pavilion
Saturday, June 20, 2026
Levitt Pavilion, Westport
Lucius brings its polished indie pop sound to an outdoor night at the Levitt Pavilion. Led by vocalists and songwriters Jess Wolfe and Holly Laessig, the band is known for close harmonies, vivid arrangements, and a dramatic live presence. The show pairs well with a summer evening for readers who want music that feels both energetic and artful.
4. Market, Wilton Farmers’ Market
Wednesday, June 17, 2026
Wilton Town Green, Wilton
The weekly farmers market returns to the heart of Wilton Center with local produce, baked goods, prepared foods, seafood, flowers, and artisan vendors. Shoppers can pick up ingredients for the week, grab lunch, and browse local makers in one easy stop. The market also includes community partners and live music throughout the season.
5. Author Talk, The Culper Ring
Tuesday, June 23, 2026
Fairfield Public Library, Fairfield
Artist Kirk Manley discusses the research and creative process behind The Culper Ring, his graphic novel and exhibition about George Washington’s spies. The talk follows his work from Revolutionary War research through rough concepts, inking, coloring, and typography. A book sale and signing follow the presentation.