Looking for things to do in Fairfield County this week and next. Late May is bringing the kind of local events that make it easy to step out close to home, from farmers markets and outdoor fairs to concerts, author talks, and time by the water. Across the county, familiar gathering places are filling up with seasonal energy and simple reasons to linger a little longer. There are easy plans for families, thoughtful programs for curious readers, and lively performances worth building an evening around. With warmer days settling in, this is a good stretch to reconnect with the places and people that make a regular week feel a little more memorable.
Across Fairfield County
1. Festival, Bruce Outdoor Crafts Festival
Saturday, May 16, 2026, and Sunday, May 17, 2026
Bruce Museum, Greenwich
Fine craft artists gather outdoors with handmade jewelry, fiber pieces, glass, pottery, housewares, and other works available to browse and purchase. Admission also includes museum access, making it an easy way to pair local shopping with time inside the galleries.
2. Family Program, Art in the Park
Saturday, May 23, 2026
Whittingham Discovery Center, Stamford
Kids and families can drop in for a hands on art program presented with the Stamford Art Association. The May 23 session focuses on a 3D carousel sculpture, with a creative project designed for all ages to make and take home.
3. Car Show, English Marques at Cars and Coffee
Sunday, May 17, 2026
Goodwives Shopping Center, Darien
Cars and Coffee Darien returns with a featured lineup of English and United Kingdom marques, from Jaguar and Aston Martin to MG, Rolls Royce, Triumph, and Land Rover. All makes and models are welcome, so visitors can expect a broader mix beyond the featured cars.
4. Concert, Chris Brubeck’s Triple Play
Tuesday, May 19, 2026
MoCA CT, Westport
Chris Brubeck performs with Peter Madcat Ruth and Joel Brown in a trio known for blending jazz, blues, folk, and classical influences. The performance brings experienced musicianship into the museum setting, with a set built around lively interplay and polished instrumental work.
5. Concert, Chris Brubeck’s Triple Play
Tuesday, May 19, 2026
MoCA CT, Westport
Chris Brubeck performs with Peter Madcat Ruth and Joel Brown in a trio known for blending jazz, blues, folk, and classical influences. The performance brings experienced musicianship into the museum setting, with a set built around lively interplay and polished instrumental work.
Greenwich Magazine
1. Greenwich Farmer’s Market Opening Day
Saturday, May 16, 2026
Arch Street and Horseneck Lane Commuter Lot, Greenwich
The season begins with local farms and food vendors returning to the commuter lot for a Saturday market. Shoppers can pick up fresh produce and seasonal goods while easing back into one of Greenwich’s familiar warm weather routines.
2. Concert, Music of America
Saturday, May 16, 2026
Greenwich Historical Society, Cos Cob
Regal Brass performs an outdoor patriotic concert with classic American songs and a lawn setting made for blankets, chairs, and picnic baskets. The program marks 250 years of American history through familiar music and a relaxed afternoon atmosphere.
3. Festival, Bruce Outdoor Crafts Festival
Saturday, May 16, 2026, and Sunday, May 17, 2026
Bruce Museum, Greenwich
Fine craft artists gather outdoors with handmade jewelry, fiber pieces, glass, pottery, housewares, and other works available to browse and purchase. Admission also includes museum access, making it an easy way to pair local shopping with time inside the galleries.
4. Festival, Cos Cob May Fair
Friday, May 15, 2026, and Saturday, May 16, 2026
Cos Cob School, Cos Cob
This annual school fair brings rides, games, and classic fair food together on the Cos Cob School field. Families can expect familiar attractions like the ferris wheel, super slide, spinning teacups, and fun house, along with pizza fritta, cotton candy, and other festival treats.
5. Garden Talk, Lush Peonies with Dan Furman
Saturday, May 23, 2026
Greenwich Botanical Center, Cos Cob
Dan Furman of Cricket Hill Garden leads a spring focused program on growing, planting, and propagating peonies. The talk includes cultivation history and a tour of the botanical center’s peony collection, with practical detail for gardeners who love big seasonal blooms.
Stamford Magazine
1. Concert, Leonid and Friends
Friday, May 15, 2026
Stamford Palace Theatre, Stamford
Leonid and Friends brings an 11 piece band to the stage with a sound built around the horn driven music of Chicago. The set also reaches into songs by Earth, Wind and Fire, Stevie Wonder, Steely Dan, and other classic artists, giving the night a polished throwback concert feel.
2. Walk, Stamford Epilepsy Walk and Purple Picnic
Saturday, May 16, 2026
Cove Island Park, Stamford
This community walk brings families, friends, and supporters together for epilepsy awareness and connection. After the walk, participants can gather for a Purple Picnic with boxed lunches, resource vendors, and a relaxed park setting.
3. Author Talk, Robert Dowling on Sam Shepard
Wednesday, May 20, 2026
Ferguson Library, Stamford
Robert M. Dowling discusses Coyote, his biography of playwright, actor, and filmmaker Sam Shepard. The conversation is moderated by Catherine Shen of Connecticut Public’s Where We Live and includes a book sale and signing with Elm Street Books.
4. Family Program, Art in the Park
Saturday, May 23, 2026
Whittingham Discovery Center, Stamford
Kids and families can drop in for a hands on art program presented with the Stamford Art Association. The May 23 session focuses on a 3D carousel sculpture, with a creative project designed for all ages to make and take home.
5. Exhibition, Likeness and Legacy
Through Monday, May 25, 2026
Stamford Museum and Nature Center, Stamford
Portraits from the permanent collection bring together paintings, prints, drawings, and sculptures connected to more than 70 years of collecting. Highlights include work tied to John Singer Sargent, Gutzon Borglum, and Soshana, along with restored pieces being shown again after decades.
New Canaan, Darien and Rowayton Magazine
1. Car Show, English Marques at Cars and Coffee
Sunday, May 17, 2026
Goodwives Shopping Center, Darien
Cars and Coffee Darien returns with a featured lineup of English and United Kingdom marques, from Jaguar and Aston Martin to MG, Rolls Royce, Triumph, and Land Rover. All makes and models are welcome, so visitors can expect a broader mix beyond the featured cars.
2. Concert, Acabella and The Conn Artists
Friday, May 15, 2026
Carriage Barn Arts Center, New Canaan
Acabella brings its women’s a cappella sound to a festive concert with an opening performance by The Conn Artists. The evening features vocal arrangements from two local groups and welcomes children 12 and under with an optional donation.
3. Author Talk, Christina Baker Kline
Tuesday, May 26, 2026
Darien Library, Darien
Christina Baker Kline discusses The Foursome, her new novel inspired by the true story of two sisters in nineteenth century North Carolina who married conjoined twins Eng and Chang Bunker. The conversation is presented with Barrett Bookstore and gives readers a closer look at the history, family ties, and moral questions behind the book.
4. Rowayton Farmers Market
Friday, May 22, 2026
Pinkney Park, Rowayton
The weekly farmers market brings local growers, food producers, and small businesses together in the park for a fresh, easygoing Friday outing. Visitors can browse seasonal goods, pick up something for the weekend, and enjoy a familiar neighborhood gathering by the water.
5. Cruise, Sheffield Island Lighthouse Excursion
Saturday, May 23, 2026, and Sunday, May 24, 2026
Norwalk Seaport Association Dock, Norwalk
This three hour excursion includes a narrated ferry ride through Norwalk Harbor and time to explore Sheffield Island. Guests can tour the historic lighthouse, take in views of the islands and shoreline, and spend part of the outing walking or picnicking by the water.
Westport, Weston and Wilton Magazine
1. Westport Farmers’ Market
Thursday, May 21, 2026, and Thursday, May 28, 2026
Westport Farmers’ Market, Westport
Local growers, food makers, and specialty vendors gather for the summer market season, with fresh produce and prepared goods from around the region. Families can browse the vendor tents, pick up ingredients for the week, and ease into the longer late spring days with a simple outing close to home.
2. Family Program, Colonial Trades Day
Saturday, May 16, 2026
Weston History and Culture Center, Weston
Visitors can step into a Revolutionary War encampment with the 5th CT Regiment and see hands on demonstrations throughout the day. The program includes soldier drills, a kid’s musket march, blacksmithing, weaving, cooking demonstrations, guided tours, and food trucks on site.
3. Concert, Chris Brubeck’s Triple Play
Tuesday, May 19, 2026
MoCA CT, Westport
Chris Brubeck performs with Peter Madcat Ruth and Joel Brown in a trio known for blending jazz, blues, folk, and classical influences. The performance brings experienced musicianship into the museum setting, with a set built around lively interplay and polished instrumental work.
4. Author Talk, Richard Bell on the Revolution
Wednesday, May 20, 2026
Wilton Historical Society, Wilton
Historian and author Richard Bell reframes the American Revolution as a global conflict with consequences far beyond the thirteen colonies. His talk follows the war’s impact across continents, including migration, antislavery activism, diplomacy, and the people whose lives were reshaped by the fight for independence.
5. Concert, Pangea Worldbeat
Saturday, May 23, 2026
StageOne, Fairfield
Pangea Worldbeat brings a genre blending sound shaped by global rhythms, danceable grooves, and a large ensemble feel. The lineup also includes The Brighton Beat and EMEFE, adding Afrobeat, brass band funk, jazz, and upbeat crowd energy to the night.