Windham doesn't have a Main Street in the way Derry or Londonderry do. What it has is Range Road, a stretch of Route 111A that's carried the town's restaurants for a decade, and 4.1 miles of paved trail that already logs the highest usage counts of any paved rail trail in New Hampshire. This year, both got busier at the same time, and the connection between them isn't a coincidence. It's a business plan.
The plainest evidence sits at 49 Range Road, where Old School Bar & Grill spent ten years as Windham's default neighborhood bar before closing for renovation and reopening this year as Becks Public House. But the more interesting fact is what came with it: Becks is the sister restaurant to Figaro's Martini Bar and Kitchen, which opened elsewhere in Windham earlier this year under the same ownership. One group, two restaurants, one town, in the same twelve months. That's not how small-town dining scenes usually expand. It's how a group expands when it thinks the town can support more than one concept at once.
A Decade-Old Bar Gets a New Chef and a New Menu
Old School Bar & Grill opened at 49 Range Road back in 2016 and spent a decade as exactly what its name promised, a straightforward neighborhood bar and grill. When it closed for renovation, the ownership brought in Chef Matthew Lavigne and rebuilt the concept from the studs up. The relaunch kept some of the old menu's anchors, including the steak tips regulars asked about by name, but the broader shift was toward what the team describes as a Boston brownstone pub feel: chef-driven comfort food, a curated beer and cocktail list, and a patio that a recent local newspaper review called impressive enough to compete with the dining room.
The kitchen kept evolving after opening. A new menu rolled out around August 3, dropping a few dishes regulars had already started to love, including a wild mushroom risotto that got singled out in that same review as worth bringing back. That's a small detail, but it tells you something about how fast the concept is still moving. Becks isn't a restaurant that opened and settled. It's still being built in public, a few weeks at a time.
The Sibling Nobody's Talking About Yet
Figaro's Martini Bar and Kitchen got its own write-up from the same paper back in May, months before Becks reopened, and the reviewer came away preferring it: smaller, more thoughtfully designed, the kind of place they said they'd go back to first. That's worth sitting with. The two most-discussed new restaurants in Windham this year aren't competitors. They're siblings, built by the same group, operating far enough apart that most residents probably don't realize they're connected until they read it somewhere.
For a town of Windham's size, that's a meaningful bet. Running two concepts under one ownership group in the same small market only makes sense if the group believes the town's dining demand has room to grow, not just shift between existing spots.
What's Actually on Range Road Now
| Restaurant | Location | What changed in 2026 |
|---|---|---|
| Becks Public House | 49 Range Road | Relaunched from the decade-old Old School Bar & Grill under Chef Matthew Lavigne, with a new menu as of early August |
| Figaro's Martini Bar and Kitchen | Windham | Opened earlier in the year under the same ownership group as Becks |
| The Windham Restaurant | 59 Range Road | No change. Still operating out of the 1812 building on a site that's held a farm or residence since 1729 |
That last row matters as much as the first two. The Windham Restaurant isn't new, isn't trying to be, and its stability is part of why the new openings read as additions rather than replacements. Range Road now has both a two-century-old anchor and two restaurants built this year around a completely different customer: the one coming off a trail, not out of a historic dining room.
The Trail Is the Real Address
Becks doesn't market itself as a restaurant near the trails. It markets itself as the reward for using them. Its own site asks visitors directly if they worked up a thirst exploring Deer Leap, Town Forest, or Fosters Pond, and frames the bar as the place to land after. That's not incidental copywriting. It's a bet that Windham's daily foot traffic runs through its trail network first and its restaurants second, and that the way to win a customer is to be the stop after the hike, not a destination on its own.
The Windham Rail Trail is the backbone that makes that bet plausible. Its 4.1 paved miles run from the Windham Depot area toward Salem, past marsh views that regulars mention in nearly every trail review, and the segment earned a Hippo Best of Best award for Best Rail Trail. Combined with the connected Derry and Salem sections, the network already offers 11 continuous miles of paved trail, one of the longest stretches of converted rail bed anywhere in the state.
That network is about to get longer. On August 17, Londonderry Trailways members Sandy Lagueux and Bob Rimol updated their town council on a project that would connect the Londonderry Rail Trail to the Derry Rail Trail, closing a half-mile unpaved gap and creating a contiguous 15-mile paved stretch running through Salem, Windham, Derry, and Londonderry, with a target completion around 2028. Rimol told the council that the Londonderry trail alone logged 51,970 visits in 2025, a daily average of 216 people, and that the numbers keep climbing.
Put those two facts together and the picture sharpens. Windham's restaurant scene isn't expanding despite the town's trail identity. It's expanding because of it, in the same year the trail itself is being formally stitched into a much bigger regional system. The businesses opening on Range Road right now are placing their bets on the same infrastructure that regional planners are actively investing in.
What Else Is on the Calendar Before the Leaves Turn
The new restaurants aren't the only thing moving in Windham this fall. A few fixtures worth having on your radar:
- Windham Country Club has charity golf events on the books this season, including an 18-hole outing on September 26 and a scramble-format fundraiser on October 24 priced at $109 per person, cart and lunch included.
- Pumpkinfest, hosted by Crossing Life Church at 122 North Lowell Road, returns for another year of hayrides, axe throwing, live music, and a craft vendor fair. The event has historically landed on the first Saturday of October, drawing families from well beyond Windham's borders.
- The Windham Museum keeps posted open hours on the town's recreation calendar throughout the fall, a quieter but steady fixture for anyone curious about the town's history beyond the Depot.
None of these are new. What's new is the density of things happening at once, on top of a dining scene that just doubled its footprint under one ownership group. Windham in early fall 2026 has more reasons to leave the house than it did a year ago, and most of them sit within a short walk or drive of each other.
The Takeaway for Anyone Who Already Lives Here
The story this year isn't that Windham got a new restaurant. Towns get new restaurants constantly. The story is that one ownership group looked at this specific town, with its trail network and its Range Road corridor, and decided it could support two new concepts at once, both explicitly built around the assumption that residents are already outside, already moving, and looking for somewhere to land. That's a different kind of confidence than a single restaurant opening on a hunch. It's a bet on the town's daily rhythm, made twice in one year, right as the regional trail system Windham anchors is getting bigger too.
If you're already living this rhythm, the practical upshot is simple: Range Road is worth a second look even if you wrote it off a decade ago as the Old School Bar & Grill strip, and the trail network you already use for a Saturday walk is about to connect to a lot more of it.
Rebecca Curran Realty works with families across Windham and the surrounding towns who want a clear read on what's actually changing on the ground, not just what shows up in a listing description. If you're curious what any of this means for your own property's value or timing, reach out and we'll walk through it together.
