
31 Connecticut Events to Enjoy in October 2021
Updated: Oct 4, 2021
Here is a list of daily events and experiences taking place in Connecticut throughout the month of October.
October 1: Crossing Delancey
Stamford
Set in New York’s Lower East side, this one-of-a-kind romantic comedy play will welcome audiences at the Dressing Room Theatre.
October 2: Atmospheric Landscapes In-Studio Workshop
Rowayton
Learn techniques to create striking paintings that capture the beauty of natural landscapes.
October 3: Fall Family Fest Sundays
Stamford
Celebrate the fall season with this weekly event that features attractions and programming for the whole family.
October 4: Minks to Sinks Sale
Wilton
Discover great finds at Minks to Sinks—from furniture and decor to clothing and jewelry at markdown prices.
October 5: Kismet Performs Live at Villa Italia
Stamford
Part of a diverse lineup of live acts at Villa Italia, the band will perform while you indulge in delicious Italian food.
October 6: Envisioning Space: Architecture through the Ages
Norwalk
This exhibit features artists’ interpretations of evolving architecture.
October 7: Restorative Yoga Class
Darien
Relax and release while performing guided deep-breathing exercises in the stunning Salt Cave of Darien.
October 8: Sheryl Crow Live
Westport
The Grammy-winning music icon will perform hits like “Soak up the Sun” and “All I Wanna Do” at the Levitt Pavilion.
October 9: Fall Family Festival
Greenwich
Perfect for the whole family, the festival offers music, vendors, and plenty of activities on the picturesque grounds of the Greenwich Historical Society.
October 10: Westport Dog Festival
Westport
Expected to attract over 1,000 dogs, this festival features competitions, obstacle courses, frisbee games, acrobatic shows, and more.

October 11: Not By the Book
Greenwich
The Flinn Gallery’s newest exhibition highlights four artists whose work celebrates the beauty and materiality of books.
October 12: Standing & Seated Yoga Practice
New Canaan
Enjoy a morning of mindfulness in nature with an outdoor yoga practice, hosted by the New Canaan Land Trust.
October 13: Knit Wits
Stratford
Join the Stratford Library’s knitting and crochet program to make friends, get tips, and share ideas for projects.
October 14: Head Over Heels
Danbury
Western Connecticut State University’s Theatre Arts department will debut this musical comedy about a royal family.
October 15: Music at MoCA: The Figgs
Westport
The beloved rock band will perform songs from their 25-year career as part of the museum’s live music series.
October 16: Scarecrow Fest
Wilton
The Wilton Center will be decorated with one-of-a-kind scarecrows designed by local residents.
October 17: Musicians from Marlboro in Concert
Greenwich
Celebrating its 57th season, the touring program will perform a special, one-night concert at the Greenwich Library.
October 18: E.T. Grab'n'go Movie Kits
Stratford
The Stratford Library is offering movie kits with everything the family could need to enjoy the classic Spielberg movie.
October 19: Greenhouse Group Fall Gardening Workshop
Darien
Sharpen your gardening skills at this engaging workshop hosted by the Darien Community Association.
October 20: Cat & Nat Reunion Tour
Ridgefield
Back by popular demand, the comedic mom duo will entertain audiences at the Ridgefield Playhouse with engaging monologues.
October 21: Suzanne Vega: An Evening of NY Songs and Stories
Ridgefield
The singer/songwriter will perform songs from her career-spanning live album at the Ridgefield Playhouse.
October 22: Mavis Staples at the Wall Street Theater
Norwalk
The acclaimed R&B and gospel singer will thrill audiences with her talents during this one-night engagement.
October 23: Oktoberfest
Rowayton
Returning for its eighth year, the fundraising event features an array of German food, brews, and plenty of live music and dancing.
October 24: Chazz Palminteri: A Bronx Tale
Ridgefield
See the iconic one-man show, which is based on a book and hit film that was also turned into a major Broadway musical.
October 25: Scary Stories to Tell in the Dark
Darien
Join Darien Library’s librarians for an evening of spooky stories on the front lawn of the Bates-Scofield House Museum.
October 26: Author Elizabeth Strout in Conversation Darien
The engagement will feature a Q&A with Pulitzer Prize-winning author Elizabeth Strout, who will detail the process behind her latest book, Oh William!
October 27: Panic in Connecticut Westport
This one-woman show sheds light on the society that condemned “witches” in CT 30 years before the Salem trials.
October 28: Gilbert Gottfried Live
Norwalk Easily one of the most recognizable voices in comedy, Gottfried will enthrall audiences at the Wall Street Theater.
October 29: New Canaan Chamber Music Fall Concert
New Canaan
Acclaimed pianist and New Canaan local Andrew Armstrong will perform alongside violinist James Ehnes.
October 30: The Monsters Ball
Rowayton
Enjoy a costume contest, live music, and more, in support of the Rowayton Historical Society’s new
Maritime Museum.
October 31: Sunday Farm Market
Stamford
The market showcases fresh produce from local farmers each Sunday at the Stamford Museum & Nature Center.