Here is the short answer on Boston Pickle Club Windsor: Boston Pickle Club is building a 37,000-square-foot, 12-court indoor club at 20 Day Hill Road in Windsor, Connecticut, just off I-91. It announced an October opening. It’s the company’s first club outside Massachusetts and its largest so far. Pre-opening memberships are on sale now, but Windsor pricing hasn’t been published.
Over the past month the pickleball business story has mostly been about clubs for sale and asking prices getting cut. So it’s worth noticing when a New England operator goes the other way. Boston Pickle Club, which runs two indoor clubs south of Boston, is crossing into Connecticut with a building bigger than either of them.
The 30-second version
- What: Boston Pickle Club’s third location. 12 indoor courts in a 37,000 sq ft building at 20 Day Hill Road, Windsor CT.
- When: announced for October 2026. The club’s site still says “coming soon” and gives no exact date.
- Extras: bar with an outdoor patio, pro shop, locker rooms with showers, players’ lounge, and a second-floor mezzanine that looks down on the courts.
- Price: not published yet. The club says Windsor pricing will differ from its Massachusetts clubs, where non-members pay a $10 day pass plus their share of the court.
- Scale: 12 courts would put it among the handful of biggest indoor rooms in Connecticut.
What is Boston Pickle Club Windsor?
Boston Pickle Club announced the Windsor club on August 18, according to the Hartford Business Journal. It will be the company’s first Connecticut location and its largest club yet. The club’s own Windsor page fills in the rest:
- 12 indoor courts with a cushioned surface and ceilings over 20 feet.
- Reception, pro shop and a full bar with an adjacent outdoor patio.
- Locker rooms with showers and a players’ lounge.
- A second-floor mezzanine with a conference room, a training area and views down onto the courts.
- Programming planned: lessons, leagues, tournaments, open play, clinics, youth programs and corporate events.
The company’s two existing clubs, both opened in 2024, are smaller: 7 courts in Hyde Park and 10 in Norwell. The company says they have more than 1,300 active members between them.
When does Boston Pickle Club Windsor open?
The announcement said October. As of this week, the club’s site still labels Windsor “coming soon” and doesn’t give a date. It has been running evening “hard hat tours” of the unfinished building to sell pre-opening memberships. People who signed up at the September 8 tour got 30% off an annual membership. If you’re in the Hartford area and thinking about joining, ask whether a pre-opening discount is still available before you pay the full rate.
We would treat “October” as a target, not a promise. Construction dates slip, and the other big Connecticut project we covered, a 19-court complex in Middletown, still has no public opening date months after its target. We’ll update this post when Windsor opens its doors.
How much will it cost to play?
Nobody outside the company knows yet. The club’s FAQ says plainly that “Windsor will have different pricing.” In Massachusetts, courts cost $35 an hour at peak and $25 off-peak, split among the players. Non-members add a $10 day pass and can book three days ahead, while members can book ten days ahead. The clubs are open 6 a.m. to 10 p.m. daily. Wait for Windsor’s posted rates before you budget.
How big is 12 courts for Connecticut?
Big. The largest indoor venues in Connecticut today have about 14 courts, and most places to play in New England have four or fewer. In our New England court directory of roughly 1,140 venues, more than two-thirds have one to four courts. A 12-court room with a bar and locker rooms is a regional draw, not a neighborhood gym.
A correction to our own directory: while checking Windsor’s existing options, we found that our listing for the town’s L.P. Wilson Community Center showed 13 indoor courts. The Town of Windsor says the facility has six outdoor pickleball courts and two tennis courts, rebuilt with $800,000 in American Rescue Plan money approved in February 2023. We’re fixing the listing. Those six free public courts and a 12-court private club will now sit in the same town.
Why expand while other clubs are for sale?
We reported this month that pickleball facilities for sale nationally have been cutting asking prices hard. Boston Pickle Club is betting the other way: a bigger building, amenities beyond the courts, and a membership base built in Massachusetts first. The project has grown on the way, too. The Business Journal says the original 2024 proposal was a 15,600-square-foot building, and the opening plan is 37,000. For more options, see our indoor pickleball in Connecticut guide and the Hartford area guide.
We have no business relationship with Boston Pickle Club. This is news coverage, not a sponsored post.
Frequently asked questions
Where is Boston Pickle Club Windsor?
At 20 Day Hill Road in Windsor, Connecticut, just off Interstate 91. It is the company’s first Connecticut location, after Hyde Park and Norwell in Massachusetts.
How many courts will Boston Pickle Club Windsor have?
Twelve indoor courts in a 37,000-square-foot building, according to the club. That’s more than its Hyde Park club with 7 courts and its Norwell club with 10.
When will Boston Pickle Club Windsor open?
The club announced an October 2026 opening in August. As of late September its website still said coming soon and gave no exact date.
Can non-members play at Boston Pickle Club?
At the Massachusetts clubs, yes. Non-members pay a 10 dollar day pass plus their share of the court and can book three days ahead. The club says Windsor will have different pricing, which it hasn’t published yet.
Is Boston Pickle Club Windsor the biggest pickleball facility in Connecticut?
Not quite. Connecticut’s largest indoor venues today have about 14 courts, and a 19-court complex is planned in Middletown. At 12 courts, Windsor will still be one of the largest indoor clubs in the state.
Sources: Hartford Business Journal, Aug. 18, 2026; Boston Pickle Club Windsor, Norwell and FAQ pages; Town of Windsor, L.P. Wilson court renovation. Verified September 2026.
