Late summer brings plenty of things to do in Fairfield County this week and next, from waterfront gatherings to live music and art. Concert lawns, museum spaces and town parks offer easy plans close to home. Families can make the most of the final August evenings with outdoor festivals, markets and hands on discoveries. Food, history and culture also give friends a reason to reconnect in familiar places. As September begins, the pace stays relaxed while local events keep the calendar interesting. A memorable outing may be closer than we think.
Across Fairfield County
1. East Coast Open Polo Returns
Sunday, August 30, 2026 Greenwich Polo Club, Greenwich The East Coast Open begins with high level polo on the club’s expansive grounds. Spectators can follow the match while enjoying food, shopping and an afternoon outdoors.
2. Stamford Summer Restaurant Weeks Begin
Monday, August 24, 2026 Participating Downtown Restaurants, Stamford Downtown restaurants introduce prix fixe lunch and dinner menus for the summer edition of Restaurant Weeks. The two week event makes it easy to revisit a favorite spot or try somewhere different.
3. Darien End of Summer Luau
Friday, August 21, 2026 Weed Beach, Darien Darien marks the season’s close with a town luau beside Long Island Sound. The waterfront setting makes it a relaxed Friday outing for families and neighbors.
4. The Short Bus Band at Waveny
Wednesday, September 2, 2026 Waveny Park, New Canaan The Short Bus Band performs familiar music spanning the 1970s through today. Families can bring blankets or chairs for this free concert on the lawn.
5. Westport Farmers Market at Imperial Avenue
Thursday, August 27, 2026 Imperial Avenue Lot, Westport Local farms and food producers gather for the market’s weekly summer session. Visitors can browse seasonal produce, baked goods, prepared foods and other locally made offerings.
Greenwich Magazine
1. Rohini Devasher Solar Poetics
Saturday, August 22, 2026 Bruce Museum, Greenwich Rohini Devasher’s first solo museum exhibition in the United States centers on an immersive work built from more than a century of solar observations. Smoke drawn copper pieces extend the artist’s study of light, astronomy and how people interpret the sun.
2. Curator Tour of Fashioning America
Saturday, August 22, 2026 Greenwich Historical Society, Cos Cob Senior Curator Kathy Craughwell Varda leads a focused tour of Fashioning America, 250 Years of Greenwich Style. The exhibition uses clothing to explore local history and changing American life.
3. America at 250 Art Exhibition
Saturday, August 29, 2026 Coffee for Good, Greenwich Artists from the Maggie Daly Arts Cooperative interpret the country’s 250th anniversary through abstract paintings and colored pencil scenes. The exhibition brings together personal views of American history, community and everyday life.
4. Sound Beach Band Plays Stephen Schwartz
Sunday, August 30, 2026 Binney Park, Old Greenwich The Sound Beach Community Band performs music by Broadway composer Stephen Schwartz in the park. The free outdoor concert offers families a relaxed way to spend a late summer evening together.
5. East Coast Open Polo Returns
Sunday, August 30, 2026 Greenwich Polo Club, Greenwich The East Coast Open begins with high level polo on the club’s expansive grounds. Spectators can follow the match while enjoying food, shopping and an afternoon outdoors.
Stamford Magazine
1. CT HorrorFest Returns to Stamford
Saturday, August 22 and Sunday, August 23, 2026
DoubleTree by Hilton Stamford, Stamford
CT HorrorFest brings horror actors, filmmakers, artists and themed vendors together for its annual convention. Panels and guest appearances give genre fans plenty to explore across the weekend.
2. OMNOM Opens The Annex Project
Sunday, August 23, 2026
The Annex Project at Stamford Town Center, Stamford
DJ and producer OMNOM headlines the first event at this new open air music venue inside the mall’s spiral garage. The gathering for guests 21 and older also includes food trucks and additional activities.
3. Stamford Summer Restaurant Weeks Begin
Monday, August 24, 2026
Participating Downtown Restaurants, Stamford
Downtown restaurants introduce prix fixe lunch and dinner menus for the summer edition of Restaurant Weeks. The two week event makes it easy to revisit a favorite spot or try somewhere different.
4. Trivia Night in Veterans Park
Thursday, September 3, 2026
Veterans Memorial Park, Stamford
Teams can test their knowledge across pop culture, sports, history and other familiar topics. Best Trivia Ever leads the questions, with prizes for the top teams and space for participants to bring their own food and drinks.
5. Explore the Nancy Grace Roman Telescope
Thursday, August 27, 2026
Stamford Museum and Nature Center, Stamford
Drop in activities introduce visitors of all ages to NASA’s Nancy Grace Roman Space Telescope. Families can explore the mission and its connection to astronomy at their own pace.
New Canaan, Darien and Rowayton Magazine
1. Darien End of Summer Luau
Friday, August 21, 2026
Weed Beach, Darien
Darien marks the season’s close with a town luau beside Long Island Sound. The waterfront setting makes it a relaxed Friday outing for families and neighbors.
2. Learning with Nature Monarch Migration
Saturday, August 22, 2026
Grace Farms, New Canaan
Grace Farms horticulture staff and experts from Kansas State University lead a field study focused on recording, tagging and releasing monarch butterflies. The workshop is recommended for ages 12 and older and includes travel across uneven terrain.
3. Pop Shop Market at Darien Commons
Saturday, August 22, 2026
Darien Commons, Darien
Independent makers gather for an outdoor market featuring apparel, jewelry, home goods, self care products and gifts. The free event gives families a casual way to browse and spend time at Darien Commons.
4. The Short Bus Band at Waveny
Wednesday, September 2, 2026
Waveny Park, New Canaan
The Short Bus Band performs familiar music spanning the 1970s through today. Families can bring blankets or chairs for this free concert on the lawn.
5. Benny and the Jets at Calf Pasture
Sunday, August 23, 2026
Calf Pasture Beach, Norwalk
Benny and the Jets closes the Third Taxing District’s summer concert series with an Elton John tribute by the water. Families can bring chairs or blankets for the free Sunday performance.
Westport, Weston and Wilton Magazine
1. The Machine Performs Pink Floyd
Friday, August 21, 2026
Levitt Pavilion, Westport
The Machine draws from Pink Floyd’s extensive catalog for an outdoor tribute concert. Detailed musicianship and a coordinated visual production recreate the scale and atmosphere of the band’s music.
2. Summer Saturdays on the Museum Commons
Saturday, August 22, 2026
Fairfield Museum Commons, Fairfield
Families can explore the Victorian Barn, Sun Tavern and Victorian Cottage while trying hands on activities across the Museum Commons. The free program shares more than 400 years of local stories, with a dedicated early childhood space available in the cottage.
3. Nature Crafts for the Whole Family
Saturday, August 22, 2026
Earthplace, Westport
Earthplace hosts a drop in nature craft with a changing weekly theme, from animal masks to butterfly projects and snake mobiles. The all ages activity is included with admission, and an Animal Hall resident may make an appearance.
4. Westport Farmers Market
Thursday, August 27, 2026
Imperial Avenue Lot, Westport
Local farms and food producers gather for the market’s weekly summer session. Visitors can browse seasonal produce, baked goods, prepared foods and other locally made offerings.
5. Cannon Grange Agricultural Fair Returns
Sunday, August 30, 2026
Cannon Grange, Wilton
The annual fair showcases horticulture, handcrafts, photography, eggs and small farm animals. Exhibits and local vendors reflect the area’s agricultural traditions in a family friendly setting.