For nearly three years, the building at 4 South Main Street sat behind plywood and a for-sale sign, a longtime fixture of the Danforth Circle reduced to a blank storefront next to the busiest intersection in town. Then this year the lights came back on. Bikes started leaning against the railing out front, still dusty from the rail trail a few blocks away. The building had reopened as Maddie's Brookside, and the people walking in for eggs and coffee were arriving on foot and by bike as often as they were pulling into the small parking lot.
That one reopening would be a nice, small story on its own. What makes it worth writing about is that it's not isolated. A years-long legal fight over how Derry's rail trail crosses the coming Exit 4A highway project just resolved in the trail's favor. Derryfest returns to MacGregor Park on September 19. And all three of these threads sit within about a half mile of each other, around the same traffic circle that Derry residents have spent a decade mostly trying to get through as fast as possible. The circle isn't just a bottleneck anymore. It's becoming the place things are happening.
The Building That Sat Empty Longest
The old Lobster Claw II closed in 2023 following the death of co-owner John Kratz Jr., and the 1,689-square-foot building sat listed for sale for months before Amanda Tomasi, a Derry resident, closed on it for $460,000. Town records show the structure dates to 1946 and cycled through a private home, a diner, and finally Lobster Claw II starting in 1986, so the building has effectively been reinventing itself at that corner for eighty years.
Tomasi already owned a Maddie's restaurant in Salem, a business she started working at as a teenager before eventually becoming its third owner. Rather than franchise the name blind, she built the Derry location from scratch and named it Maddie's Brookside, a nod to West Running Brook flowing behind the property. She told the Union Leader the move was about getting to know her own town differently: "It will help me get to know the community at a different level." The restaurant now serves breakfast and lunch daily, and reviewers on local platforms have specifically called out how close it sits to the rail trail behind downtown, the kind of foot traffic a seafood restaurant built for dinner crowds never had.
That detail matters more than it looks. A restaurant surviving on trail walk-ins instead of only drive-up dinner reservations is a different kind of business than the one that used to occupy that space, and it only works because of what's happening two blocks away.
The Highway Project That's Also Saving the Trail
Derry's Exit 4A expansion on I-93 has been talked about locally mostly as a headache. The town's own Public Works Director warned in 2024 that the project could bring significant traffic disruption for at least three years once construction began in 2025, and the town moved up unrelated paving work specifically to avoid stacking multiple construction zones on top of each other.
What's less understood is that the same project is the reason the Derry Rail Trail may finally connect north to Londonderry, a goal the Derry Rail Trail Alliance has been chasing since the trail first opened. The original Exit 4A plan called for a tunnel carrying trail users safely under the new six-lane interchange. In 2022, the New Hampshire Department of Transportation reversed course and proposed a cheaper alternative nicknamed the "spaghetti loop," a design that would have forced trail users off the railbed, through a series of steep turns, and across a six-lane intersection instead of under it.
The Derry Rail Trail Alliance didn't let it go quietly. In 2024, a newly formed Committee to Save the Derry Rail Trail joined with the national nonprofit Rails to Trails Conservancy to file a legal complaint arguing the new design violated federal historic preservation protections, since the trail runs along a former Boston and Maine Railroad corridor. In June 2025, a federal judge agreed, ruling against the state's design and effectively forcing NHDOT back to the original tunnel plan. Trail advocates and the state have been working out construction details since.
Cathy McDonald, a volunteer with the Alliance, described what's at stake for a commuter town wedged along I-93: "In the car, people can be very aggressive. On the trail, people wave and say hello to you." The Rails to Trails Conservancy named the Derry trail its November 2025 Trail of the Month largely on the strength of that story.
Here's where the pieces stand right now:
| Segment | Length | Status |
|---|---|---|
| Derry Rail Trail (Hood Park to Windham line) | About 3.6 miles, paved | Open |
| Windham Rail Trail (connects south) | About 4 miles, paved | Open |
| Derry to Londonderry connection | Unpaved gap | Tunnel design confirmed, construction pending under Exit 4A |
The unpaved gap that's held up a full Derry-to-Manchester trail corridor for years is finally moving, and it's moving because of the same highway project residents have been dreading.
What's Actually at Derryfest This Year
Derryfest returns to MacGregor Park on Saturday, September 19, with the day built around live music, food vendors, and local craft and community booths, the same format that's made it Derry's largest single-day gathering for years. Parking is spread across downtown's municipal lots, with additional overflow at Grinnell Elementary School on Grinnell Road and legal street parking along East Broadway.
The festival sits close enough to downtown that it's realistic to walk from the trail or from the Danforth Circle corridor rather than drive in, which matters more this year than most, given how much attention the traffic circle and Exit 4A corridor have already absorbed.
One Half-Mile, Three Storylines
None of these three things caused the others. Maddie's Brookside opened because one Derry resident wanted to build something new in a building that had outlived its old purpose. The tunnel ruling happened because volunteers spent years in court and at town hall meetings over a trail corridor most drivers never think about. Derryfest happens every September regardless of what else is going on downtown.
But they're converging on the same half-mile stretch of town right now, and that's worth noticing if you live here. The corner everyone used to just drive through now has a reason to stop. The trail everyone assumed would dead-end at a highway crossing has a legal path forward. And the festival that's always been Derry's biggest gathering falls smack in the middle of both stories, walking distance from each.
Downtown Derry isn't being rebuilt by one developer or one plan. It's being rebuilt by a restaurant owner, a volunteer trail alliance, and a town calendar that happened to line up this particular September. That's a slower kind of change than a ribbon cutting, but it's the kind that tends to stick.
If you're watching how Derry's downtown corridor is shifting, whether you're a longtime resident curious about what's next or thinking ahead to your own next move in southern New Hampshire, Rebecca Curran Realty keeps a close eye on the towns we work in, not just the listings in them. Reach out anytime you want a local read on what a corner like this one actually means for the neighborhood around it.
