Chester's Sunday farmers market held its last regular day of 2026 on October 11, after 18 weeks on Main Street. It returns as a smaller Holiday Market on November 29. Between those dates, the town's official 2026 events schedule lists only two things: the downtown Halloween event and the Veterans Day ceremony.
For those seven weeks, the calendar is kept on Main Street by a brewery, a new coffee and cocktail bar, a bookshop, and a makers' space. The two calendars start to overlap again on November 29 and line up completely on one Sunday in December.
Who is hosting what, week by week
The town schedule covers the civic events: road closures, the Chester Hose Company, and the Veterans and American Legion ceremony. Everything else comes from individual businesses. Laid out by date, you can see who is doing the hosting.
| Date | What's happening | Host |
|---|---|---|
| Fri, Oct 23 | Halloween Carnival and Main Street trick-or-treating, 6 to 8:30 p.m. | CES PTO |
| Sat, Oct 24 | Third Annual Adult Costume Contest, 7 to 8:30 p.m. | Little House Brewing |
| Thu, Oct 29 | Halloween Beer & Cheese Pairing with Mystic Cheese, 6 to 9 p.m. | Little House Brewing |
| Thu, Nov 5 | Paint & Sip, 6 to 8 p.m., $25 | Little House Brewing |
| Fri, Nov 6 | First Friday with Tucker Oyster Co. and Steve Harz | Little House Brewing |
| Sat, Nov 7 | Free Meat Raffle, 2 to 5 p.m. | Little House Brewing |
| Wed, Nov 11 | Veterans Day Ceremony, 11 a.m. | Chester Veterans and American Legion |
| Sun, Nov 29 | First Holiday Sunday Market; Foam & Fables book club | Chester Marketplace; Little House and Montgomery & Taggert |
| Fri, Dec 4 | First Friday Holiday Lights pop-up; Steve Harz live | The Hive; Little House Brewing |
| Sun, Dec 6 | Holiday Market; monthly Open Mic | Chester Marketplace; Little House Brewing |
| Sat, Dec 12 | Seed&Stone pop-up, noon to 4 p.m. | Little House Brewing |
| Sun, Dec 13 | Holiday Market; Dee's Blind Dates book pop-up | Chester Marketplace; Little House Brewing |
| Sun, Dec 20 | Final Holiday Market; She's Crafty pop-up; Santa Comes to Town | Chester Marketplace; Little House Brewing; Chester Hose Company |
One address shows up more than any other. Little House Brewing's events calendar has about a dozen dated events at 16 Main Street between late October and New Year's, plus free weekly trivia that runs into the last week of December. As a result, from the end of the market to the start of the holiday season, much of Chester's public calendar runs through a single taproom.
Halloween weekend starts the handoff
The town-scale event comes first. The Chester Elementary School PTO runs its Halloween Carnival on Friday, October 23, from 6 to 8:30 p.m., with Main Street trick-or-treating, food, music, and games. The PTO's page says there will be no cemetery walk this year. On the town schedule, the Halloween event is one of the few in the second half of the year that closes downtown streets.
The next night, the same weekend continues on a smaller scale. Little House holds its Third Annual Adult Costume Contest on Saturday, October 24, from 7 to 8:30 p.m. The following Thursday, October 29, it pairs beer with Mystic Cheese from 6 to 9 p.m. The carnival is the town-run event. The two nights after it are the first examples of businesses hosting on their own.
November is mostly at 16 Main Street
Once Halloween is over, the town schedule has one civic event before Thanksgiving. The Veterans Day Ceremony is Wednesday, November 11, at 11 a.m. near the War Memorial at Route 154 and Railroad Avenue. It's coordinated by Chester Veterans and the American Legion with the First Selectman's Office.
Most other dated events that month happen at the brewery. Paint & Sip is Thursday, November 5, from 6 to 8 p.m., with tickets listed at $25. November's First Friday falls on November 6. Tucker Oyster Co. shucks oysters from 5 to 7 p.m., and Steve Harz plays from 6:30 to 8:30 p.m. The free meat raffle follows on Saturday, November 7, from 2 to 5 p.m.
The month ends with a collaboration across Main Street. Foam & Fables, a book club run by Little House and Montgomery & Taggert, meets Sunday, November 29, from 4 to 6 p.m. at Montgomery & Taggert, 26 Water Street, then moves to Little House for drinks. It lands on the same day the Holiday Market returns, the first time since Halloween weekend that the business calendar and the town calendar share a date.
Three Fates covers the rest of the day
The brewery calendar mostly runs in the evenings and on weekend afternoons. Chester's newest stop covers the hours before and after. Three Fates opened in 2026 at 1 North Main Street. CT Insider announced it in December 2025 as a planned coffee and wine bar from Tiffany Nevers. Edible CT East's September profile describes it as a coffee, wine, and cocktail bar serving locally roasted coffee, matcha, boutique wines, and cocktails from a mixologist, with a seasonal food menu.
The E List's June review gave these hours:
- Monday and Tuesday: closed
- Wednesday and Thursday: 8 a.m. to 10 p.m.
- Friday and Saturday: 8 a.m. to 11 p.m.
- Sunday: 9 a.m. to 3 p.m.
Hours often change once the weather turns, so check the bar's own channels before going. As listed, though, the Sunday hours cover the full 10 a.m. to 1 p.m. Holiday Market window. The same review mentions small plates such as mortadella sliders, empanadas, and smoked trout rillettes, plus a gin, blueberry, and lavender cocktail. On a First Friday or a market Sunday, Three Fates and Little House give Main Street two hosts at opposite ends of the block.
The market comes back smaller, and December 20 brings everything together
The holiday version of the market is much shorter than the summer season. The regular market ran 18 Sundays from June 14 to October 11. The Holiday Sunday Markets run four: November 29 and December 6, 13, and 20, each from 10 a.m. to 1 p.m. The summer market closed downtown streets. On the town schedule, the holiday market is marked "Roads remain open." The Chester Sunday Market's holiday page says regular market vendors will be joined by additional sidewalk vendors.
December's First Friday is the 4th. The Hive at 1 Maple Street lists its First Friday Holiday Lights Edition that evening, a holiday shopping pop-up with local makers, seasonal treats, and live music. The listing gives the time as 8 to 9 p.m. Steve Harz plays at Little House that same night from 6:30 to 8:30 p.m.
The busiest single day of the season is Sunday, December 20. The town schedule describes Santa's visit as falling on the "last Sunday before Christmas," which also makes it the final Holiday Market. The day runs in this order:
- 10 a.m. to 1 p.m.: the last Holiday Sunday Market of the year, with roads open.
- Noon to 4 p.m.: She's Crafty sells upcycled and vintage glass candles at Little House Brewing, 16 Main Street.
- 5 to 7 p.m.: Santa Comes to Town, hosted by Chester Hose Company.
The town schedule doesn't give a street address for the Santa visit, but it does list it as a downtown road-closure event. It's the only day since August when the town calendar and the business calendar fully overlap: the market, a maker pop-up, and the fire company's event on Main Street in a single afternoon and evening.
If your weekend includes the river crossing
The Chester-Hadlyme Ferry runs from April 1 through November 30, except Thanksgiving, according to the Connecticut Department of Transportation. That means a cross-river plan around Thanksgiving weekend fits inside the season, but the December 20 day does not. The ferry was out of service for part of September. LymeLine reported that the Selden III went to drydock for maintenance and seal replacement, with service expected back around mid-September depending on the repairs. CTDOT posts closures during the season on CTroads, and that is the place to check before driving down to the landing.
A replacement vessel is planned. In August, Governor Lamont announced $6.4 million in federal funding and $1.6 million in state funding for a diesel-hybrid ferry to replace the Selden III, which has worked this route since 1950. NBC Connecticut reported in September that DOT had not yet set a timeline for designing and building it.
Once the last Holiday Market wraps up on December 20, spring is the next season on the calendar. If your plans for it include your own house on or near Main Street, The Nancy Mesham Team can give you a clear, local read on its current value. Ask us: What is my home worth?
