Things to do in Fairfield County this week and next make it easy to enjoy October without going far. A favorite place can feel completely different when there is live music on the lawn, a new exhibit inside or a fall festival filling the grounds. Families have plenty of reasons to get outside, while workshops and performances offer easy plans for adults too. Some outings can fill an afternoon, while others are just enough to break up the week. That variety is part of what makes this time of year so enjoyable here. A good October plan may be closer than you think.
Across Fairfield County
1. Greenwich Historical Society Fall Harvest Festival
Saturday, October 10, 2026
Greenwich Historical Society, Cos Cob
The annual celebration brings seasonal activities, games and food to the historical society campus. Families can spend the afternoon enjoying fall traditions and exploring the grounds together.
2. Luckypawlooza Festival at Mill River Park
Saturday, October 10, 2026
Mill River Park, Stamford
Lucky Dog Refuge brings its annual community festival back to the park with adoptable dogs, vendors, food and activities. The outdoor event welcomes families and dog lovers while supporting the rescue’s work.
3. First Annual Fall for Darien
Saturday, October 10, 2026
Highland Farm, Darien
Darien welcomes the season with live music, family activities and local vendors at Highland Farm. The free, all ages gathering offers an easy way to spend a fall afternoon together.
4. 314 Oktoberfest at the Beer Garden
Sunday, October 11, 2026
314 Beer Garden, Norwalk
The beer garden marks Oktoberfest with seasonal food, drinks and live entertainment. The outdoor gathering brings a festive fall atmosphere to South Norwalk.
5. Rachs Hope Walk the Extra Mile
Sunday, October 4, 2026
Compo Beach, Westport
The community walk brings people together in support of families navigating serious illness and other difficult circumstances. Participants can enjoy the shoreline route while helping a local organization provide practical assistance.
Greenwich Magazine
1. Greenwich Historical Society Fall Harvest Festival
Saturday, October 10, 2026
Greenwich Historical Society, Cos Cob
The annual celebration brings seasonal activities, games and food to the historical society campus. Families can spend the afternoon enjoying fall traditions and exploring the grounds together.
2. Greenwich Symphony with Cellist James Baik
Saturday, October 3 and Sunday, October 4, 2026
Performing Arts Center at Greenwich High School, Greenwich
Cellist James Baik joins the Greenwich Symphony Orchestra for Shostakovich’s Cello Concerto No. 1. The program also includes works by Adolphus Hailstork and Nikolai Rimsky Korsakov.
3. Into the World of Autumn Mushrooms
Saturday, October 3, 2026
Greenwich Botanical Center, Cos Cob
Explore the biology, folklore and everyday uses of mushrooms with naturopathic physician and educator Dr. Lindsay Chimileski. A guided walk around the grounds offers a closer look at fungi growing in the local landscape.
4. 45th Annual Outdoor Arts Festival
Saturday, October 10 and Sunday, October 11, 2026
Bruce Museum, Greenwich
Artists from around the country display original paintings, sculpture, photography and mixed media throughout the museum grounds. Festival admission also includes entry to the Bruce Museum, making it easy to explore both indoor exhibitions and outdoor art.
5. Hawk Watch Fest at Greenwich Audubon Center
Saturday, October 3, 2026
Greenwich Audubon Center, Greenwich
Meet live hawks and owls while learning about the journeys birds of prey make each fall. Naturalist led workshops, birding activities and live music make this an engaging day for families and longtime bird watchers alike.
Stamford Magazine
1. Stayin Alive Bee Gees Tribute
Friday, October 2, 2026
The Palace Theatre, Stamford
Stayin Alive recreates the sound and style of the Bee Gees with a full evening of familiar hits and ballads. Large screen visuals accompany songs including Night Fever, Jive Talkin and How Deep Is Your Love.
2. Trail Sessions Hike and Concert
Saturday, October 3, 2026
Bartlett Arboretum and Gardens, Stamford
Bartlett staff lead a gentle guided hike through the gardens and trails before an outdoor performance by Connecticut indie pop band Similar Kind. The combination offers a relaxed way to enjoy both the landscape and live local music.
3. Stamford Downtown WineFest on Bedford
Saturday, October 3, 2026
Latham Park, Stamford
WineFest brings a selection of wines to the heart of downtown Stamford for an afternoon tasting. Guests can explore different pours while enjoying the setting along Bedford Street.
4. Meet Authors Tessa Wegert and Joanna Margaret
Saturday, October 10, 2026
Ferguson Library, Stamford
Connecticut authors Tessa Wegert and Joanna Margaret visit the library for a conversation about their latest work. The program gives local readers a chance to hear directly from two writers and learn more about their creative process.
5. Luckypawlooza Festival at Mill River Park
Saturday, October 10, 2026
Mill River Park, Stamford
Lucky Dog Refuge brings its annual community festival back to the park with adoptable dogs, vendors, food and activities. The outdoor event welcomes families and dog lovers while supporting the rescue’s work.
New Canaan, Darien and Rowayton Magazine
1. Painting Music Experience at Carriage Barn
Saturday, October 3, 2026
Carriage Barn Arts Center, New Canaan
Cellist Sophie Shao performs as contemporary artist Vincent Inconiglios creates visual art inspired by the music. The program offers a close look at how two different art forms can respond to one another in real time.
2. Our Town by Thornton Wilder
Saturday, October 3 through Sunday, October 18, 2026
Powerhouse Theatre at Waveny Park, New Canaan
The Town Players of New Canaan stage Thornton Wilder’s Pulitzer Prize winning portrait of everyday life in a small American town. The production follows the joys, routines and losses shared by two neighboring families.
3. Needlepoint a Holiday Ornament Workshop
Thursday, October 8, 2026
The Mather Homestead, Darien
Participants can begin a hand stitched holiday ornament during this seasonal homesteading workshop. Materials are provided, and the finished project offers a personal addition to holiday decorating or gift giving.
4. First Annual Fall for Darien
Saturday, October 10, 2026
Highland Farm, Darien
Darien welcomes the season with live music, family activities and local vendors at Highland Farm. The free, all ages gathering offers an easy way to spend a fall afternoon together.
5. 314 Oktoberfest at the Beer Garden
Sunday, October 11, 2026
314 Beer Garden, Norwalk
The beer garden marks Oktoberfest with seasonal food, drinks and live entertainment. The outdoor gathering brings a festive fall atmosphere to South Norwalk.
Westport, Weston and Wilton Magazine
1. Westoberfest Craft Beer and Fall Festival
Saturday, October 3, 2026
Sigrid Schultz Plaza, Westport
Downtown Westport fills with craft beer tastings, live music, food and seasonal activities for the ninth annual Westoberfest. Family activities run alongside the ticketed tasting area, giving all ages a way to join the afternoon.
2. Earthplace Fall Festival 2026
Saturday, October 3, 2026
Earthplace, Westport
The annual festival brings families together for nature based activities and seasonal fun across the Earthplace grounds. Explorer wristbands provide access to special activities, while the sanctuary and animal hall add more to discover.
3. Rachs Hope Walk the Extra Mile
Sunday, October 4, 2026
Compo Beach, Westport
The community walk brings people together in support of families navigating serious illness and other difficult circumstances. Participants can enjoy the shoreline route while helping a local organization provide practical assistance.
4. Art in Focus David Roberts
Thursday, October 8, 2026
Fairfield University Art Museum, Fairfield
An informal gallery conversation takes a close look at David Roberts’ The Hypostyle Hall. The focused format invites visitors to slow down, notice details and learn more about a single work on display.
5. Gemstone Sparkle Sprint 5K
Saturday, October 10, 2026
Gemstone Farm, Wilton
Runners and walkers travel through the private 150 acre Gemstone Farm during this community 5K. The scenic course offers a different way to enjoy Wilton’s fall landscape while supporting the Prospector Theater.