As October gives way to November, there are plenty of things to do in Fairfield County this week and next. The season is changing quickly now, and crisp afternoons and earlier sunsets can make even familiar places feel a little different. This is a good time to try somewhere new, return to a favorite local venue or turn an ordinary weekend into something more memorable. Bring family or friends, or claim a few hours for yourself. Nothing requires a long drive or an elaborate plan. Pick what fits the mood and enjoy being close to home.
Across Fairfield County
1. Silver Shield Foundation Greenwich Walk
Saturday, November 7, 2026
Tod’s Point, Old Greenwich
The community walk honors fallen police officers, firefighters and EMS members while supporting educational assistance for their children. Participants can enjoy the waterfront route while helping families across the region.
2. Stamford Baptist Church Fall Festival
Saturday, October 31, 2026
Stamford Baptist Church, Stamford
Families can spend Halloween evening enjoying games, activities and seasonal fun together. The annual gathering is open to all ages.
3. Halloween Spooktacular at Nature Center
Friday, October 30, 2026
New Canaan Nature Center, New Canaan
Spiders, snakes, owls and other animal ambassadors set the scene for a nature inspired Halloween evening. Families can make crafts, roast marshmallows, share stories around the campfire and follow a jack o lantern walk.
4. CraftWestport Fine Craft Festival
Saturday, November 7 and Sunday, November 8, 2026
Staples High School Field House, Westport
More than 175 artists and makers display jewelry, ceramics, glass, textiles, sculpture, photography and other original work. Families can browse together, with free admission available for children under twelve.
5. Willie Nile Full Band Concert
Thursday, November 12, 2026
StageOne at Fairfield Theatre Company, Fairfield
Buffalo born singer and songwriter Willie Nile returns to Fairfield with his full band. His guitar driven catalog blends New York rock, melodic songwriting and stories drawn from a career spanning several decades.
Greenwich Magazine
1. Screenagers Generation AI Community Screening
Thursday, November 5, 2026
YWCA Greenwich, Greenwich
A screening explores how artificial intelligence is shaping the ways young people learn, connect and create. Youth panelists and representatives from OK to Delay lead a discussion after the film.
2. Silver Shield Foundation Greenwich Walk
Saturday, November 7, 2026
Tod’s Point, Old Greenwich
The community walk honors fallen police officers, firefighters and EMS members while supporting educational assistance for their children. Participants can enjoy the waterfront route while helping families across the region.
3. Greenwich Symphony with Albert Cano Smit
Saturday, November 7 and Sunday, November 8, 2026
Performing Arts Center at Greenwich High School, Greenwich
Pianist Albert Cano Smit joins the Greenwich Symphony Orchestra for Grieg’s Piano Concerto. The program also includes Don Juan by Richard Strauss and Borodin’s Symphony No. 2.
4. Better with Butter Homemade Butter Workshop
Sunday, November 8, 2026
Greenwich Historical Society, Cos Cob
Visitors can make homemade butter while learning how the kitchen staple was prepared in earlier eras. Family friendly tours and a hands on activity offer ways for all ages to explore the historical society campus.
5. Paperwhites and Amaryllis Walk Up Bulb Bar
Wednesday, November 11 and Thursday, November 12, 2026
Greenwich Botanical Center, Cos Cob
Visitors can pot paperwhites or amaryllis in a container brought from home or purchased at the center. Botanical center staff provide guidance for creating a seasonal arrangement to keep or give as a gift.
Stamford Magazine
1. America The Happy Trails Tour
Friday, October 30, 2026
The Palace Theatre, Stamford
Classic rock band America brings five decades of music to the stage on its Happy Trails Tour. The set draws from a catalog that includes A Horse with No Name, Ventura Highway and Sister Golden Hair.
2. Stamford Baptist Church Fall Festival
Saturday, October 31, 2026
Stamford Baptist Church, Stamford
Families can spend Halloween evening enjoying games, activities and seasonal fun together. The annual gathering is open to all ages.
3. Hunger for Truth Documentary Screening
Sunday, November 1, 2026
Ferguson Library, Stamford
Andrew Tkach’s documentary follows journalist Rhea Clyman’s reporting on the Holodomor and her journey through the Soviet Union during the 1930s. Archival material is paired with contemporary stories from Ukraine.
4. Bartlett Holiday Gift Sale
Saturday, November 7 and Sunday, November 8, 2026
Bartlett Arboretum and Gardens, Stamford
Holiday ornaments, pottery, jewelry, books, toys and handcrafted pieces fill the Silver Educational Center for this community sale. Items are donated by Bartlett volunteers and Master Gardeners, with proceeds supporting educational programs at the arboretum.
5. Oliver at Curtain Call
Friday, October 23 through Saturday, November 14, 2026
The Kweskin Theatre, Stamford
Lionel Bart’s musical follows a young orphan through the streets of Victorian London. Familiar songs and a large ensemble bring Charles Dickens’s story to the local stage.
New Canaan, Darien and Rowayton Magazine
1. Halloween Spooktacular at Nature Center
Friday, October 30, 2026
New Canaan Nature Center, New Canaan
Spiders, snakes, owls and other animal ambassadors set the scene for a nature inspired Halloween evening. Families can make crafts, roast marshmallows, share stories around the campfire and follow a jack o lantern walk.
2. Run with the Saints 5K
Sunday, November 1, 2026
Saint Luke’s Parish, Darien
Runners can choose a chip timed 5K along Darien’s coastal roads, while children and walkers can join the one mile route. Registration supports charitable outreach programs serving communities throughout Fairfield County and beyond.
3. The Beatles The Music That Shaped Art Style and Culture
Sunday, November 1, 2026
Carriage Barn Arts Center, New Canaan
Music, film clips, album artwork, photography and fashion trace the visual influence of The Beatles. Presented by New Canaan native Eliot Goldberg, the multimedia program concludes with a live performance of Beatles songs.
4. The Wrecks Finally Outside Tour
Wednesday, November 4, 2026
District Music Hall, Norwalk
Worry Club and Kid Sistr join The Wrecks for a midweek concert in downtown Norwalk. The all ages show brings three current rock bands together on one bill.
5. Amanda FitzSimons and An American Girl
Thursday, November 12, 2026
Barrett Bookstore, Darien
Journalist Amanda FitzSimons discusses her new book about Pleasant Rowland and the creation of the American Girl brand. The conversation considers the dolls’ influence on girlhood, history and American culture.
Westport, Weston and Wilton Magazine
1. Pippin at The Wilton Playshop
Friday, November 6 through Saturday, November 21, 2026
The Wilton Playshop, Wilton
A young prince searches for an extraordinary life in Stephen Schwartz and Roger O. Hirson’s musical. The local production combines a familiar score with theatrical storytelling and is best suited to older audiences because of its mature themes.
2. CraftWestport Fine Craft Festival
Saturday, November 7 and Sunday, November 8, 2026
Staples High School Field House, Westport
More than 175 artists and makers display jewelry, ceramics, glass, textiles, sculpture, photography and other original work. Families can browse together, with free admission available for children under twelve.
3. Canoe Paddle on the Saugatuck
Sunday, November 8, 2026
Earthplace, Westport
An Earthplace naturalist leads families and friends along the Saugatuck River by canoe. Paddlers can watch for osprey, egrets, turtles and other wildlife while exploring the local waterway.
4. Anthony Ratinov Sunday Soundscapes Concert
Sunday, November 8, 2026
Weston Public Library, Weston
Prize winning pianist Anthony Ratinov introduces the library’s new Estonia grand piano with a preview of his upcoming Carnegie Hall recital. The performance opens the new season of the Sunday Soundscapes concert series.
5. Willie Nile Full Band Concert
Thursday, November 12, 2026
StageOne at Fairfield Theatre Company, Fairfield
Buffalo born singer and songwriter Willie Nile returns to Fairfield with his full band. His guitar driven catalog blends New York rock, melodic songwriting and stories drawn from a career spanning several decades.