Festive & Fabulous Fall Happenings in October

October is a time to enjoy the best of the fall season in Ridgefield! Join us for festive happenings, fabulous arts and culture performances, spooky celebrations, and all things pumpkin spice during this colorful season #inRidgefield.

Annual Giant Pumpkin Weigh-Off

Annual Giant Pumpkin Weigh-off & Festival

Sunday, October 1st – NEW DATE!
Ballard Park

This year’s 11th Giant Pumpkin Weigh Off will feature giant pumpkins, live music, enjoy local vendors, farm animals, children’s activities, and more! The Annual Giant Pumpkin Weighoff is presented by the Connecticut Giant Pumpkin Growers Club.

2nd Annual Blueprints & Blue Jeans Fall Fundraiser

Wednesday, October 4th
The Ridgefield Playhouse

This gala supports Habitat for Humanity’s 31 years of building homes, communities, and hope in the Western Connecticut region. The event is hosted by comedian Christine O’Leary with entertainment by guest auctioneer Max Tucci and music by local musician Jim Endee. The evening will feature food and cocktails, silent auctions, and more.

High School Admissions Fair

Wednesday, October 4th
Ridgefield Academy

Ridgefield Academy is pleased to host one of the largest high school fairs in the region. We invite all to come learn about the many independent day and boarding school options for high school. This event is open to the public, no RSVP required.

History on Tap

Friday, October 6th
Keeler Tavern Museum & History Center

Back for a second year in a row, History on Tap is a fun and casual evening of beer tastings, delicious food, live programming, and a historical drink-making demonstration.

Ridgefield Farmers Market

Saturday, October 7th & 21st
Jesse Lee Church

Join us for the Ridgefield Farmers Market to enjoy goods from local farms, food trucks, makers, and musicians every other Saturday. Pack your picnic blanket and enjoy shopping and eating with the best local vendors! The last day of the Ridgefield’s Farmers Market will be October 21st, 2023.

Oktoberfest 2023

Saturday, October 7th
Nod Hill Brewery

Oktoberfest Season kicks off at Nod Hill Brewery in Ridgefield! Come down for a liter of Festbier or Old Homeplace and pair it with a currywurst from Walrus Alley. Join us to range of German-inspired beers poured by the liter, featuring Festbier, Old Homeplace, Giddyup, Dabulous, Diamant, Shazau, Altbier and more.

Revolutionary Ridgefield Bus Tour

Saturday, October 7th
Hosted by the Ridgefield Historical Society

Enjoy an afternoon on a bus tour exploring colonial Ridgefield. Learn about the architecture, people, and stories connected to these historic places. The tour will explore a great collection of some 20 of these places. Several stops will allow interior visits.

Family Workshop and Tours: Indigenous Peoples’ Day

Monday, October 9th
The Aldrich Contemporary Art Museum

Come for a special day of tours and art-making inspired by the colossal sculptures of Raven Halfmoon. Join us for Museum Educator guided tours of Raven Halfmoon’s exhibition Flags of Our Mothers, then stay to create coil pots with self-dry clay in the Studio. Tours will be offered at 1 pm and 3 pm.

Fall In Love With Ridgefield

Saturday, October 14th
Downtown Ridgefield

Join us for a beloved town tradition and enjoy face painting, balloon artists, music, pumpkin painting, specials at our local shops, and more. We can’t wait to see you there!

Art in the Park Festival

Saturday, October 14th
Weir Farm National Historical Park

The Art in the Park Festival will include art demonstrations, activity stations, free-to-use art supplies, refreshments, live music, and more! The park welcomes artists, neighbors, national park lovers, and visitors of all ages to participate.

College Essay Writing Workshops

Saturdays, October 14th – December 9th
First Congregational Church Ridgefield & Hotel Zero

An “Ace the Essay” workshop can help your high school student make a bigger impression with admission officers by combining the power of personal brand marketing with powerful writing strategies on their college essay. Choose from any one of nine convenient workshop dates.

Kindergarten – Grade 4 Open House

Sunday, October 15th
Ridgefield Academy

Experience all that Ridgefield Academy’s 42-acre campus has to offer with a nature walk, food science activity in the Kitchen Lab, and by exploring their state-of-the-art Outdoor Campus Center.

Sunset Wine Party

Friday, October 20th
Lounsbury House

Get ready to experience Fairfield County’s one and only wine shopping event and fundraiser for ArtFul Visual Arts Initiative. Taste over 70 wines at the MINI of Fairfield Grand Wine Tasting Room and sample decadent bites from our dedicated grazing table.

Third Saturdays

Saturday, October 21st
The Aldrich Contemporary Art Museum

Visit the Museum for FREE the third Saturday of every month as part of our Third Saturdays program. Participate in a Story Time at 10:30 am, a Discovery Tour of Raven Halfmoon, Yvette Mayorga, Chiffon Thomas, and Ping Zheng’s exhibitions at 1 pm, and drop-in to The Studio for art-making activities.

“Sunset Boulevard”

Opens Saturday, October 28th
ACT of Connecticut

Sunset Boulevard tells the magnificent tale of Norma Desmond, a faded silent-screen goddess living in her mansion clinging to a fantasy that audiences still long for her, but in reality, hardly remember her. This Tony Award winning masterpiece has been called Andrew Lloyd Webber’s finest scores and weaves a compelling tale of romance, obsession, and faded glory.

Ghosts of Ridgefield

Friday, October 27th – Sunday, October 29th
Keeler Tavern Museum & History Center

Traverse the museum’s site and meet the ghosts of some of Ridgefield’s former residents who are eager to share their stories with passersby. For 2023, ghosts include an artist, an anti-book banning activist, a Tory woman, and an Italian immigrant entrepreneur – take the tour to find out more!

All Hallow’s Gala

Friday, October 27th
Lounsbury House

Join us for a night of wonder and intrigue! This annual fundraising Gala is a festive and fun cocktail-style event that includes drinks, dancing, delectable hors d’oeurvres, dramatic decor, live auction, costume contests, photo booth and more.

Ridgefield’s Halloween Walk

Saturday, October 28th
Main Street in Ridgefield

Join us for Ridgefield’s Annual Halloween Walk on Saturday, October 28th from 10am-12pm. Bring the kids to enjoy trick-or-treating in their Halloween costumes at the shops in Downtown Ridgefield!

Ridgebury Farm Fall Festival

Saturday, October 28th
Ridgebury Farm and Stables

Come out to the farm for fall fun! Pumpkin picking, hay rides, and yard games galore – visit the farm for a day of fun for the whole family.

Jesse Lee Pumpkin Patch

Through Tuesday, October 31st
Jesse Lee Church

A favorite town tradition, the Annual Pumpkin Patch will be open from September 30th – October 31st! Bring the family to pick out your perfect pumpkin for decorating or carving this year.

Trunk or Treat

Tuesday, October 31st
Lounsbury House

Join us for Trunk or Treat with Ridgefield Police Department on October 31st from 5pm – 8pm at Lounsbury House! This is a free event intended for families and children up to 12 years old.

At the Galleries:


Save the dates!
Holiday Boutique in the Barn – Begins November 16th
Festive Home – Begins November 18th
Ridgefield’s Annual Tree Lighting – Friday, November 24th
Ridgefield Holiday Stroll – December 1st & 2nd


For all the latest events in Ridgefield, visit our Events Calendar and follow us at @inridgefield!