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


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


Learn techniques to create striking paintings that capture the beauty of natural landscapes.

October 3: Fall Family Fest Sundays


Celebrate the fall season with this weekly event that features attractions and programming for the whole family.

October 4: Minks to Sinks Sale


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


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


This exhibit features artists’ interpretations of evolving architecture.

October 7: Restorative Yoga Class


Relax and release while performing guided deep-breathing exercises in the stunning Salt Cave of Darien.

October 8: Sheryl Crow Live


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


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


Expected to attract over 1,000 dogs, this festival features competitions, obstacle courses, frisbee games, acrobatic shows, and more.

Wilton - Scarecrow Fest
Wilton's "Scarecrow Fest" Will Take Place Oct. 16

October 11: Not By the Book


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


Join the Stratford Library’s knitting and crochet program to make friends, get tips, and share ideas for projects.

October 14: Head Over Heels


Western Connecticut State University’s Theatre Arts department will debut this musical comedy about a royal family.

October 15: Music at MoCA: The Figgs


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


The Wilton Center will be decorated with one-of-a-kind scarecrows designed by local residents.

October 17: Musicians from Marlboro in Concert


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


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


Sharpen your gardening skills at this engaging workshop hosted by the Darien Community Association.

October 20: Cat & Nat Reunion Tour


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


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


The acclaimed R&B and gospel singer will thrill audiences with her talents during this one-night engagement.

October 23: Oktoberfest


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


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


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


Enjoy a costume contest, live music, and more, in support of the Rowayton Historical Society’s new

Maritime Museum.

October 31: Sunday Farm Market


The market showcases fresh produce from local farmers each Sunday at the Stamford Museum & Nature Center.

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