Memorial Field was supposed to be full on Sunday, October 4, with New Fairfield Fair Day running from noon to 4:30. It stayed empty. The rain had soaked the fields so badly that the town said they could not safely hold the heavy trucks, equipment and vendor vehicles a fair needs. Driving onto the grounds could have damaged the park and made it unsafe for everyone there. The cancellation notice on the town calendar gives no makeup date, and none appears on the November calendar either.
So this year, the one big open-field gathering is off the fall calendar. What's left between now and Thanksgiving weekend is a set of smaller events at specific addresses, most of them on Route 37. Each one has its own limit. The concert has a fixed number of seats. The new restaurant closes at 7. The holiday shop may not be back in its building next year. If you plan around those limits, the rest of the fall in town goes much more smoothly.
The lake side has already shut for the season
The pull toward Town Center starts at the water. Connecticut DEEP closes Squantz Pond State Park to vehicles from fall through spring. You can still park at the boat launch and walk in, but the park bathrooms closed after Labor Day. Candlewood Kayak Rentals is down to weekends and holidays, and posts its hours ahead of time.
That leaves the walk-in route along Squantz Pond for a quiet weekday morning. For anything else on the calendar between now and the end of November, head to Route 37.
The addresses that hold the rest of the fall
Here are the places that come up again and again through the end of November:
- Town Hall, where the Selectmen hand out the first treat at Tricks and Treats Fest
- 11 Route 37, Legacy Dance Center's studio
- 25 Route 37, Burger Barn, in the old Olde 37 Patio & Grill space
- 33 Route 37, the New Fairfield Senior Center, home of Groovin' in New Fairfield
- 84 Route 37, The Christmas Cottage
- 100 Route 37, Bruno's Pizza, Pasta & Catering
- 1 Brush Hill Road, The Mail Drop
- 54 Gillotti Road, New Fairfield High School, the one big venue off this stretch, for the 5K the Sunday before Thanksgiving
Most of the season happens within that short list of Route 37 numbers.
Halloween week runs on two different clocks
The first event is Friday, October 23. St. Edward's Parish holds its Trunk or Treat at 6:30 p.m.
The town's own Halloween event comes six days later. New Fairfield Parks & Recreation's annual Tricks and Treats Fest is Thursday, October 29, from 4:30 to 6:00 p.m. Kids pick up a treat bag and their first treat from the Selectmen in front of Town Hall. Then they work through the participating businesses on the event map. At 5:30, Legacy Dance Center leads a "ghoulish thriller dance" at its studio at 11 Route 37.
The window is only 90 minutes, and it starts at 4:30 on a school-and-work Thursday. Because the dance is set for 5:30, families who want to see it have to be at the studio halfway through the hour and a half. Start at Town Hall right at 4:30, visit the businesses near the studio before the dance, and save the rest of the map for after it.
Dinner can stay on the same road. Burger Barn at 25 Route 37 is open Wednesday through Sunday, noon to 7 p.m., so on Fest night it closes about an hour after the treat route ends.
The newest room on Route 37 closes at 7
Burger Barn is the newest business here this fall. CT Insider reported that it held its grand opening on October 1 in the former Olde 37 Patio & Grill space, after a late-summer soft opening used for menu testing and setting up ordering. Chef-owner Justin Heitmann and his business partner, Kiera Mejia, now have online ordering running. "The whole town has taken to the place, it's great," Heitmann told CT Insider.
The menu is handcrafted smash burgers and specialty hot dogs the restaurant calls "dirty dogs." Options run from classic dogs to the Fusion Dog, with garlic aioli, kimchi, scallions and sesame seeds, and The Figgy Pig, with cream cheese, fig jam and bacon jam.
The hours matter for planning. Burger Barn is closed Monday and Tuesday and stops serving at 7 the rest of the week, so it works for a late lunch or an early dinner. For a later meal, or a night it's closed, Bruno's Pizza, Pasta & Catering at 100 Route 37 offers dine-in, takeout and catering.
Saturday, November 7: a concert with a seat limit
Bruno's also caters the most planned-ahead night of the month. Groovin' in New Fairfield presents Canadian roots and blues singer-songwriter Suzie Vinnick, with special guest John Fries, at the New Fairfield Senior Center, 33 Route 37, on Saturday, November 7. Doors open at 6:45 p.m. and the show starts at 7:30. Every seat is $15. Vinnick is a three-time Juno Award nominee who has won 12 Maple Blues Awards.
Of all the fall events here, this is the one where the room size matters most. You can buy tickets in advance at the Senior Center, or by mail with cash or a check. The organizers ask anyone planning to buy at the door to call 203-746-1142 first, to make sure the show hasn't sold out. If you're mailing a check, they ask you to allow enough time and to include your name, address, phone and email.
Before the show there's a moderately priced dinner catered by Bruno's Restaurant. The choices include Eggplant Rollatini, Chicken Francese, pizza, salad and homemade desserts, and you can refill your own reusable water bottle for free. Since doors open 45 minutes before showtime, dinner and the concert fit in one trip to 33 Route 37.
Groovin' is a nonprofit funded by sponsors, local businesses and grants from charitable contributions. It has already posted its 2027 lineup: Luke Brindley with special guest Sarah Mac on January 30, Griffin Anthony on September 18, and David Jacobs Strain on November 6.
Four days later, on Wednesday, November 11, the town calendar lists the New Fairfield Veterans Day Ceremony at 11 a.m.
The holiday shop may be in its last season at 84 Route 37
Holiday shopping in town also has a deadline this year. The Town Tribune reports that The Christmas Cottage at 84 Route 37 is open Monday through Saturday, 10 a.m. to 3 p.m. It's the seasonal extension of The Mail Drop at 1 Brush Hill Road. This is the Cottage's second year, and the owners told the paper they expect it to be the last one at this address because the building is for sale.
The two shops split the season. The Cottage carries the decorating and gift stock, including nutcrackers, ornaments, linens, nativity sets, advent calendars, blankets, gloves, hats, robes, jewelry, mugs and candles. The main Christmas toy shop is at The Mail Drop. That's where toddlers will find a ride-on train, a ball pit and a playhouse, and older kids get a floor piano and a Nerf target practice station. There are free cookies every day.
The Town Tribune says about 90 percent of the items are $50 or less. The Cottage's clearance room runs on its own schedule. Jewelry there and skinny scarves are $1, cocktail and wine glasses are $5 each, and everything else is half off until the week before Christmas, when it all drops to $1.
The Mail Drop also helps with holiday shipping. It handles FedEx, UPS and USPS drop-offs and full-service shipping, and it sells boxes and packing supplies. It only accepts labels with barcodes, though. Its software can't process QR codes or Happy Returns, so print a barcoded label before you go. It doesn't offer notary services.
With both shops closing at 3 p.m. and closed Sundays, weekday commuters will need a Saturday to shop there.
The Sunday before Thanksgiving belongs to Gillotti Road
The one big event this fall that isn't on Route 37 is the 42nd annual Run for the Turkeys. New Fairfield Parks & Recreation holds the 5K road race and health walk on Sunday, November 22, at New Fairfield High School, 54 Gillotti Road. Race bibs go out starting at 9 a.m., the Kids Fun Run starts on the high school track at 9:30, and the race starts at 11 a.m. sharp.
The 5K costs $27.50 on RunSignup, including a $2.50 fee. The Parks & Recreation flyer asks everyone to bring a non-perishable food item for the NF Social Services Food Pantry. The three best Thanksgiving costumes win prizes, there's music along the course, and spectators are welcome. The deadline to guarantee a race shirt order is November 6, the day before the Groovin' show.
The season ends on Thanksgiving weekend. Santa's Workshop, the Holiday Light Parade and the Tree Lighting are on the town calendar for Saturday, November 28, with Sunday, November 29, as the rain date. As of this week, the town's event listing still says "Details to come," with no time or location posted yet. Given how October 4 went, keep both weekend days open until the town posts details.
Our team keeps up with what opens, closes and changes hands along Route 37 because many of our clients ask us about it first. If a new business or a sign on a familiar building has you wondering what's next for Town Center, Dvora Price and The Price Team are always glad to talk it over. When you're ready to look closer to home, Get Access To Our Listings.
