Ridgefield's October Starts and Ends on Main Street. The Middle Belongs to Its Museums and Stages.

On Saturday, October 3, the last Ridgefield Farmers Market of the season, the Giant Pumpkin Weigh-Off and the Chamber's Fall in Love with Ridgefield all take place on the same stretch of Main Street. Twenty-eight days later, on Saturday, October 31, the town's Halloween Walk brings families back to the same sidewalks. Downtown has the busiest days at the start and end of the month. Most of the calendar in between belongs to The Aldrich, Keeler Tavern, the Ridgefield Playhouse, A.C.T. of Connecticut and Weir Farm.

That pattern is useful for planning. The free street events are at either end of October, and most of the ticketed, reserve-ahead events fall between them.

Saturday, October 3, hour by hour

Three anchor events overlap that morning, along with smaller programs from the Library and The Aldrich. The outdoor ones line up along Main Street, from Jesse Lee Greens at 207 Main to Ballard Park at 485 Main.

The farmers market closes at 1 p.m., and its 2026 season, which opened June 20, ends with it. That makes the morning the last chance to buy from those vendors until next year. The weigh-off runs later. Growers unload from 9:30, but the Great Pumpkin Commonwealth's schedule puts the actual weighing at noon, which leaves one hour of overlap with the market before the scale has Ballard Park to itself through the afternoon.

The Chamber's own lineup for the downtown portion includes live music by Bob Stump "Tree-Oh," playing blues, bluegrass and Americana, plus face painting, fall photo spots and the scarecrow contest. The Library's Costume Swap is the one free event that day that requires registration, and the Library says you don't need to bring a costume to take part. Co-Create at The Aldrich combines a gallery visit with a paper light-sculpture workshop. It costs $47.70 per child, which includes one adult, plus $21.20 for each additional adult, and pre-registration is required.

What actually happens at the weigh-off

The Connecticut Giant Pumpkin Growers Club hosts the weigh-off, and the event listing notes it was rescheduled to October 3. The Ridgefield Herald lists public admission as free. The $25 fee and the September 24 registration deadline applied only to growers entering a pumpkin.

It is a sanctioned competition under Great Pumpkin Commonwealth rules. Pumpkins, squash, watermelons, bushel gourds, field pumpkins, marrows and tomatoes get official weights, long gourds are measured for length, and plaques and ribbons go out after the weighing. Pumpkins and squash must arrive on a pallet. The organizers' listing also promises music, farm stands, farm animal exhibits and children's activities. According to this year's event preview, the Ridgefield record belongs to Tony Ciliberto, whose pumpkin weighed 2,352.5 pounds. That's the number every grower on the scale is trying to beat.

Parking on a Ballard Park Saturday

There's no published street-closure notice or shuttle plan for October 3, so parking works the way it normally does, with more cars. The town identifies three municipally owned downtown lots: behind Town Hall, part of the Bailey Avenue lot, and the Governor Street lot.

• Governor Street lot. Between RVNA and the Boys & Girls Club, this is the town's listed free all-day lot and the simplest choice if you plan to stay from the market through the weigh-off.
• Bailey Avenue and Town Hall. Both are east of Main Street and close to the center of the Chamber's activity.
• West of Main. The visitor guide lists a municipal lot west of Main Street near Ballard Park and another south of the park near CVS.
• Library and Prospector lots. Library visitors can use the lot by the Main Street entrance or the adjacent Prospector Theater lot off Prospect Street, which is convenient for the 1 p.m. Costume Swap.

The two published sources don't fully agree on weekend parking rules. The visitor guide describes no weekend restrictions, while the Parking Authority says it enforces at large Ballard Park events. Posted lot signs are the ones to follow on October 3.

Sunday, and the Main Street shop behind the wine party

The weekend continues into October 4. Keeler Tavern Museum & History Center holds its free First Sunday from 11 a.m. to 4 p.m., with apple-themed crafts and no advance registration. That evening, Lounsbury House at 316 Main Street hosts the Sunset Wine Party from 6 to 8 p.m. It features more than 60 wines, grazing boards, a Sparkling Lounge and music, and all proceeds support the historic house.

Sommlike powers the event, and its role shows how Main Street changed this year. Sommlike held its grand opening at 407 Main Street on June 19, 2026. Co-founders Paula Alonso Perez and Nicholas Ktorides run it as a wine and spirits shop that also hosts tastings. Less than four months after opening, the shop is pouring at one of the town's preservation fundraisers alongside Mini of Darien, The Chefs' Warehouse and other sponsors.

Main Street lost an address this season too. Patch reported in August that Tequila Escape, open at 439 Main Street since 2019, had closed. Its farewell thanked Ridgefield for letting the restaurant be part of the community, and no plans for the space have been announced. Outside downtown, Riko's Pizza held its grand opening on July 30 at 955 Ethan Allen Highway, with a full bar, an outdoor patio and private event space.

The middle weeks move to the institutions

After the first weekend, the scarecrows stay up around town through November 1, but most of the calendar moves into galleries, theaters and the woods. Here's the order it runs in:

1. October 9. An RSO Quartet concert inspired by The Aldrich Decennial starts at 7 p.m. at The Aldrich. Tickets are $37.50 for members and $42.50 general admission.
2. October 10. Ridgefield Theater Barn's run of DISASTER! the Musical closes. Weir Farm National Historical Park, at 735 Nod Hill Road in Wilton, offers its Second Saturday Stone Wall Tour at 10 a.m.
3. October 17 and 18. This is the busiest middle weekend, and it centers on art. The Aldrich's Community Day runs 10:30 a.m. to 5 p.m. with free admission and a 2 p.m. performance by exhibiting artist Anindita Dutta. Ballard Park hosts the Ridgefield Fall Arts Festival with 100 juried artists, organized by Gordon Fine Arts with the Ridgefield Arts Council and the Ridgefield Guild of Artists. One local calendar lists Saturday hours of 10 a.m. to 5 p.m. Sunday hours and admission haven't been posted. Weir Farm leads guided fall hikes from 9:30 to 11 a.m. both mornings.
4. October 22. A.C.T. of Connecticut opens Beautiful: The Carole King Musical at 36 Old Quarry Road, running through November 22.
5. October 23 to 25. Ghosts of Ridgefield runs from 5 to 7 p.m. each night at Keeler Tavern, with tickets at $30 for adults and $15 for children. Dar Williams plays the Playhouse on October 23 at 8 p.m.
6. October 25. 123 Andrés – ¡No Tengo Miedo!, a bilingual Halloween concert where costumes are welcome, is at 2 p.m. at the Playhouse. Weir Farm's Take Part in Art watercolor session runs from 1 to 4 p.m.
7. October 28. Pianist Emanuel Ax performs at 7:30 p.m. at the Playhouse.

Two longer exhibitions run through the whole month. The Aldrich Decennial: I am what is around me continues in the galleries and sculpture garden through January 10, 2027. General admission is $20 for adults, $15 for seniors and $9 for students, and admission is free on Third Saturdays. Keeler Tavern's interactive Hands-On History: Living Off the Land is in the Carriage Barn through November 1, Thursday to Sunday, 11 a.m. to 4 p.m.

One mid-month event connects to the end of the month. Ridgefield Parks & Recreation's free Halloween Window Painting on October 17 has middle and high school students painting downtown storefronts from 10 a.m. to 2 p.m., and registration closes October 10. Those windows will still be up when trick-or-treaters arrive two weeks later.

October 31 brings the crowds back downtown

Halloween falls on a Saturday this year, and the day comes in two parts. The Town of Ridgefield's Halloween Walk runs from 10 a.m. to noon on Main Street, with trick-or-treating at downtown shops. That evening, Lounsbury House's October calendar lists Trunk or Treat from 5 to 8:30 p.m. It's free, outdoors only, open to children of all ages, and hosted by the Ridgefield Police Department. The separate event page still shows last year's date, so check with Lounsbury House before you go. A.C.T.'s 2 p.m. performance that day is sensory-friendly and closed to the general public.

The month officially wraps on Sunday, November 1. Keeler Tavern holds another free First Sunday from 11 a.m. to 4 p.m. At 2 p.m., the Playhouse hosts Meet the Orchestra with the Western Connecticut Youth Orchestra, followed by an instrument "petting zoo." The scarecrows come down that day too.

If your fall weekends in Ridgefield have you wondering what a home closer to Main Street, or farther out toward Weir Farm, would mean for your daily routine, Randy Musiker is happy to talk it through.