2025 Darien Fall Fun Guide: Oktoberfest, Pumpkin Painting, And More

DARIEN, CT — The autumnal equinox on Monday, Sept. 22, signals the official arrival of fall, but the season is already in full swing in Darien with several events.

Sunny days and crisp evenings are perfect for outdoor fun. One can’t-miss event is the second annual Oktoberfest event which supports the Darien Chamber of Commerce.

But that’s just the beginning of fun activities taking place over the next couple of months.

Are you planning an event this fall? Feature it so nearby readers see it all across Patch — including in roundups like this!

Below, find the 2025 Patch Guide to Fall Fun in and around Darien:

• 2nd Annual Oktoberfest in Darien: The event on Oct. 4 will feature live music, games, traditional Bavarian food and drink, and German-style craft beer. Food will be prepared by Michael Joseph’s, beer provided by Sly Bandit Brewing Company, and wines and cocktails curated by Sipstirs. Entertainment will be provided by the band Something Fried.
• Pumpkin Paint Party at Darien Commons: Grab the kiddos and join us at Darien Commons on Sunday, October 5 from 12–3pm for our first-ever Pumpkin Paint Party!
• Stamford Town Center Fall Festival: On Oct. 12, enjoy live music, seasonal treats, games, and activities for all ages. It's the perfect way to embrace autumn in downtown Stamford.
• Ken Burns new cinematic documentary: The American Revolution Exclusive CT Preview: The Mather Homestead in partnership with CT Public on Oct. 14 will host an exclusive preview of Ken Burns’ long awaited documentary series "American Revolution." This six part series premiers in November and examines how America's founding turned the world upside down.
• Tokeneke School Pumpkin Carnival: Scheduled for 10 a.m. to 4 p.m. at 7 Old Farm Road in Darien, Tokeneke Elementary School will be transformed into a Halloween-themed festival and amusement park. The event will feature a variety of lawn games, art activities, face painting, and prizes as well as many Darien restaurants.
• 2025 Fall Harvest Festival at The Mather Homestead: On Oct. 25, families can enjoy pony rides, hayrides, a petting zoo, pumpkin decorating, face painting, games, live music, and seasonal treats like cider and donuts.
• Stamford Town Center Halloween Candy Crawl: On Oct. 26, put on your favorite costume and join the fun at the Halloween Candy Crawl! Trick-or-treat at participating retailers, enjoy games and activities, and meet costumed characters throughout the center. It's a spook-tacular day for families and kids of all ages.