For a while, the box at 500 Bushy Hill Road sat the way empty retail spaces do. A HomeGoods sign came down, the windows went dark, and the plaza known as Simsbury Commons had one more storefront waiting for a tenant. A few miles away, a narrow shopfront on Railroad Street sat next to Plan B restaurant with nothing in it worth walking past for.
Both spaces are full now. Neither filled with what you'd expect, and neither needed a single new building to do it.
A Big Box Built For A Chain, Filled By Paddles Instead
The old HomeGoods footprint is nearly 24,000 square feet, the kind of space that only a handful of tenants in Connecticut could realistically fill. What moved in was Dill Dinkers, an indoor pickleball club that turned the empty box into seven courts, six of championship size and one standard, all under one roof and all playable in any weather, any season.
Simsbury wasn't a random pick. The club is the flagship for a group planning up to ten Dill Dinkers locations across Connecticut, and it's run in part by Max Johnson, a Simsbury native who partnered with three other Connecticut residents to buy the franchise rights for the state. The group calls itself the Pickleball Brothers.
"We are thrilled to be on our way to opening one of the first indoor pickleball clubs in Simsbury," Johnson said when the club was announced. "It's more than just a business to us."
What's easy to miss from the outside is what the climate control actually changes. Simsbury already has outdoor courts, but those come with a season attached. A club built inside a former big box doesn't. It's open daily, year-round, staffed by a dedicated pro and director, and it runs leagues and lessons on a reservation system rather than a first-come basis. For a sport that's grown fast nationally, that's a meaningfully different commitment than painting some lines on an existing court.
A Storefront Easy To Walk Past If You Weren't Looking
Sycamore Vintage Home Goods opened February 1 at 2 Railroad Street, in a space small enough that you could miss it if Plan B next door weren't already on your radar. It's the newest venture from Katie and Shawn Damon, an Avon couple who spent years collecting before deciding to sell.
The inventory on opening day gives a sense of the shop's range: Polish pottery, vintage art, bakeware and stoneware, a spice rack and jars, plant charms, figurines, teapots and creamers, even a vintage copy of Hemingway. It's the kind of stock that produces a specific reaction from browsers, the one Katie Damon says she hears most.
"My grandma had that."
That line is the whole pitch. Sycamore isn't trying to be a design showroom. It's positioned as a place where someone finds an object they recognize from a relative's kitchen, priced low enough to take home on impulse. Damon has described the sourcing philosophy as built around sustainability and accessibility, the idea being that one-of-a-kind pieces shouldn't come with a one-of-a-kind price tag.
Same Problem, Two Different Sizes
Put the two side by side and a pattern shows up that's easy to miss if you only hear about one of them. A national retailer walked away from a nearly 24,000 square foot box, and what replaced it wasn't another chain trying the same format. It was a club built around people showing up in person, repeatedly, to play. A small storefront on a side street sat empty with no obvious next tenant, and what filled it wasn't a franchise at all. It was two people who wanted to sell things they'd spent years finding.
Neither required new construction. Neither needed the town to approve a subdivision or a new commercial building. Both took existing square footage, at opposite ends of the size spectrum, and bet that people in Simsbury wanted a reason to leave the house and be around each other, whether that's on a court or in front of a shelf of Polish pottery.
For a town that's largely built out, that's the version of growth that actually shows up. Not cranes, but tenants.
Quick reference if you're planning a visit:
- Dill Dinkers Simsbury – 500 Bushy Hill Road, Simsbury Commons plaza. Open daily, indoor courts, leagues and lessons available by reservation.
- Sycamore Vintage Home Goods – 2 Railroad Street, next to Plan B restaurant. Vintage housewares, rotating inventory, opened February 2026.
What It Means For A Simsbury Weekend
Neither of these openings changes anything about home values or school enrollment or the things that get measured in a market report. What they change is smaller and more immediate: two more default answers to the question of what to do on a Saturday that didn't exist a couple of years ago, both born from filling space that was already there rather than building something new.
That's worth noticing on its own terms, not because it signals anything about where Simsbury is headed, but because it's already true. The town's newest gathering spots are inside buildings you'd have driven past without a second look.
We watch these shifts closely because they're part of what makes a town feel like itself, long before anyone starts thinking about buying or selling here. If you're weighing what life in Simsbury actually looks like day to day, or you're ready to talk through a move in either direction, Lisa Sweeney Team is glad to help. Request a confidential consultation whenever the timing is right.
