Chatham MA Off-Season Things to Do: New Gathering Places

Chatham's October calendar is full, and all of it ends by November 1. The pumpkin patch, the displays in Kate Gould Park, Oktoberfest and the Witches Walk all run on fixed end dates. After that, the town's social life moves indoors to a handful of rooms. Several of them didn't exist two winters ago.

Five businesses that opened in 2025 or 2026 now shape what a Chatham week looks like from November to spring: a café and bistro on Main Street, a sports bar, a mahjong shop, a coffee roaster on Crowell Road and a coffeehouse on Seaquanset Road. Their posted hours and holiday plans make up the off-season calendar. On September 29, the Select Board also showed that neighbors help set those hours.

October runs on a countdown

The month is crowded, and almost every item on it has an end date. The town's October 2 Mainsheet and the Select Board's September 29 licensing votes give the schedule.

Some of these have changed. The Chatham Chamber of Commerce and Merchants Association renamed its Kate Gould Park display Pumpkinpalooza in the Park. The new name reflects a move beyond pumpkin "people" to a wider range of creative displays, and entries were still open when the October 2 Mainsheet went out. This year's Oktoberfest has two stages of live music, food trucks and tents, beer, wine and cider, an Artist Village and a Kid Zone. The Witches Walk, run by Monomoy Community Services, starts at Chatham Cookware on the evening of October 24.

Once the pumpkins come down in Kate Gould Park on November 1, there's no shared town event on the schedule. Weekly routines take over.

The rooms that carry the weeks after

None of these five businesses is a summer-only stand. Each one has published year-round hours, off-season programming or holiday service. The Cape Cod Chronicle's 2025 year-end review listed Three Fins Coffee Roasters and Hey Joe and Jam among the businesses that opened in 2025. Main Street Mahjong opened in November 2025. TK's Sports Bar followed in April 2026, and Beacon & Buoy was scheduled to open in June. For most of them, this is their first or second winter.

Beacon & Buoy, 1200 Main Street. This café, provisions shop and bistro is in the former Chatham Cut space and is led by Executive Chef Melissa Ramsay. Axios reported in May that it planned to open in June. Its OpenTable listing shows service daily from 11:30 a.m., with last seating at 10 p.m. That listing comes from a third party, so confirm hours with the restaurant as the season changes. Beacon & Buoy also says outright that it plans for winter. Its events page describes a lineup of seasonal and themed events for the local community "through the quieter shoulder seasons and into the winter months," and says bookings and details are coming soon.

TK's Sports Bar, 1077 Main Street. TK's opened in April 2026, according to Axios. The town's February hearing notice shows it as a new business name for Uncle Tony's LLC, the company behind the former Knot's Landing Bar & Grill, so this is a rebrand of a familiar location rather than a sale. The Chronicle has identified Trish Kennedy as co-owner. The bar's site says "Every day is Gameday." Its new fall schedule lists Monday, Wednesday and Thursday from 4 to 10 p.m., with Tuesday closed. Weekend hours aren't shown in the posted text, so check before a Sunday game.

Main Street Mahjong, 726 Main Street. Jill Boudreau's shop opened in November 2025, just as the season was ending. A few months later she told the Chronicle, "I am having a ball meeting great people!" Posted hours are Wednesday through Saturday from 11 a.m. to 5 p.m. and Sunday from noon to 5 p.m. Tuesdays are by appointment and Mondays are closed. The shop offers Mahjong 101 and 102 lessons at $50 each and hosts private parties. The October 2026 page of its open-play calendar was up but showed no listed sessions when we checked, so ask the shop directly about drop-in tables.

Three Fins Coffee Roasters, 251 Crowell Road. The business describes itself as a coffeehouse and cacao factory and posts daily hours of 7 a.m. to 4 p.m. It sells hands-on sessions, including a $40 Brewing Methods class and a $65 roasting demonstration that was sold out when checked. Dates aren't posted. It also hosted an event on March 21, 2026, which shows the space is used well outside summer.

Hey Joe and Jam, 16 Seaquanset Road. This creative coffeehouse serves espresso drinks, tea and café food along with house-made jams. Posted hours are Wednesday through Saturday from 7 a.m. to 4 p.m. and Sunday and Monday from 7 a.m. to 1 p.m., with Tuesday closed. Its live-music listings ran on weekends through Saturday, September 26. Then the Select Board took up its license.

The vote that set Hey Joe and Jam's music hours

On September 29, the Select Board heard a request from This Is My Jam LLC, which does business as Hey Joe and Jam. The business wanted to widen the permitted hours on its annual entertainment license to 10 a.m. to 10 p.m. Under the current license, entertainment was limited to a morning window plus one night a month from 7 to 9 p.m. The town's October 2 Mainsheet recorded the result:

After hearing from the applicant and neighboring residents in opposition to the expanded hours, the Select Board voted to amend the 2026 entertainment license to restrict the hours to 10 hours per week between 10:00 a.m. to 8:00 p.m.

The vote gave the coffeehouse more than it had: evening music is now possible on more than one night a month. It also set two limits. Music has to end by 8 p.m., and the weekly total is capped at 10 hours. For anyone planning around live sets on Seaquanset Road this winter, that means a shorter, earlier schedule than the one requested. The site's events page showed no dates past September 26 when checked, so an updated lineup under the new terms will be the thing to watch for.

The vote also shows how Chatham's off-season hours get set. A new business can apply for later hours. The board weighs that request against the people who live next door, in a public hearing on a Tuesday evening at the Town Office Annex. The final schedule came from that hearing.

The holidays are already on the calendar

The clearest evidence of a winter plan is a holiday menu, and Beacon & Buoy has posted two. Its Thanksgiving 2026 offering is a chef-prepared meal for home pickup on Wednesday, November 25. The restaurant will close Thanksgiving Day and reopen Friday, November 27. Its site also has a page for Christmas Eve 2026. A kitchen that plans that far ahead expects to be cooking for people in Chatham in late November and December.

Put those dates next to the October table and the off-season starts to take shape. The pumpkins come down on November 1. Thanksgiving pickup is at 1200 Main Street on November 25. Every week in between and after has its own regular stops: coffee on Crowell Road or Seaquanset Road, a lesson at the mahjong table, a weeknight game at 1077 Main Street. The Chatham Squire at 487 Main Street is also on the October 20 hearing list for a change of manager on its liquor license.

All of the hours above were posted by the businesses or listing services, and most pages show no update date. Before you plan an evening around them, confirm by phone or check the business's own page.

Chatham's winter calendar affects more than where to eat. It matters when you plan when a house is lived in, rented or listed. If you'd like to talk about how the year-round side of town fits your plans for a home here, the team at Cape Island Estates is in Brewster and happy to help. You can also start with a free home valuation.