As N Magazine reported, when Riley moved to Nantucket in 2021, one of his first stops was Tom Nevers Field. He found a baseball diamond that had gone to seed, the kind of neglect that happens when a field outlives whatever demand originally justified it. He was devastated by the state of it, but he could not stop thinking about what the place could become. Four years later, in the fall of 2025, he posted on Facebook asking if anyone wanted to meet up and play catch. The response surprised him enough that he teamed up with Bret Samboy, a former SUNY Albany first baseman who had spent years commuting off-island to play for teams like the East Boston Knights, and the two of them started building something.

That something is now the Nantucket Island Men's Senior Baseball League, and it launched its first season this past April with more than 75 members. But the story of that field does not start or end with Riley and Samboy. It runs through a softball league that has quietly met there every summer Sunday for more than a decade, a September fair that turns the same grass into a working country fairground, and a Cold War bunker still sitting under all of it. For a neighborhood with no restaurant row, no market, and no walkable center, that one field is doing the work that a town square does everywhere else on the island.

A Field With Two Different Baseball Communities

The Nantucket Island Men's Senior Baseball League is new, but it did not appear out of nowhere. Roughly two-thirds of the 75-plus members who signed up for tryouts came from the Dominican Republic, many of them men who had spent years playing in a different league on the same field: the Dominican Softball League, which has run on summer Sundays at Tom Nevers for more than a decade.

Samuel Taveras, a carpenter who moved to Nantucket from the town of Cabrera in the Dominican Republic, has played in that Sunday league for years. For him, the game is less about competition than continuity, a way of keeping a piece of home alive on an island three thousand miles from it. When Riley and Samboy started organizing tryouts for the new fast-pitch league, players like Taveras were a natural bridge between the two.

The two leagues do not compete for the same nights. The established softball league holds its Sunday-afternoon slot, roughly 50 men strong, a tradition long enough that most of the neighborhood has stopped noticing it as anything unusual. The new league claims Friday and Saturday nights, plus Sunday doubleheaders, a schedule that turns Tom Nevers Field into the busiest patch of grass in the neighborhood three days out of every seven, all summer.

What It Took to Get the Field Back

Getting the diamond back into shape was not a quick fix. It took what Riley later described as hundreds of hours of work, some from the league's own volunteers and some from the town, before the field was playable again. That kind of turnaround does not happen for a field nobody cares about. It happens because a neighborhood without a center still needs somewhere to gather, and this was the one piece of shared ground Tom Nevers had.

The town has separately been trying to expand what the field can support. Nantucket's Parks and Recreation department has discussed plans to prepare the Tom Nevers softball and baseball fields to eventually house Nantucket Little League, while using the Nobadeer fields as a temporary home for youth lacrosse during the transition. Getting there involves the unglamorous work of rebuilding soil and irrigation systems, since a proper grass field takes a minimum of two growing cycles to establish. None of that is finished, but it points to the same pattern: whatever recreational infrastructure Nantucket adds to its south side keeps landing at Tom Nevers, because there is nowhere else on that end of the island with the space for it.

One Weekend a Year, the Fairgrounds Earn the Name

For one weekend in September, the same field switches identities entirely. This year's Nantucket Island Fair took over the grass on September 12 and 13, running 10 a.m. to 4 p.m. both days, with admission set at $30 per car and $10 for walkers and bikes.

The fair leaned into an old-fashioned country format rather than a carnival one. Ray's Barnyard set up in the livestock tent with alpacas, donkeys, goats, pigs, chickens, rabbits, and ducks. The community tent ran judged competitions for a Tar Roof Cake contest and a best-cookie contest, alongside a fairy house competition split by age group. The county fair games moved through the day on a fixed schedule: an inflatable obstacle course to open, a sack race, a three-legged race, a watermelon-eating contest at noon, a cupcake-eating contest, a water balloon toss, and a hot pepper-eating contest before the day closed with a skillet toss. Off to the side, in the section of the property still called the Fairgrounds, there were disc golf demonstrations, scarecrow building, and a dunk tank sponsored by the Knights of Columbus.

It is worth remembering that this section of the field carries that name, Fairgrounds, for a reason that predates the current fair by decades. Long before the Nantucket Island Fair existed in its current form, the same stretch of grass hosted informal ball games between island teams with names like the Natives and the Siasconsets, going back to at least the 1870s. This year's fair, like the ones before it, picked back up on ground that had already been doing this kind of work for more than a century.

What Sits Underground While All This Happens

Beneath the outfield grass and somewhere near the fair's livestock tent sits a structure most fairgoers walk right past: a partially buried Cold War bunker built in the early 1960s as an evacuation shelter for President John F. Kennedy, in case a nuclear exchange with the Soviet Union caught him at his family's Hyannisport compound. Kennedy never visited it. The Navy decommissioned the surrounding facility in 1976, and the bunker eventually became the headquarters of the Nantucket Hunting Association starting in 1995, a role it has held ever since.

In 2023, the National Park Service included the Tom Nevers bunker among two dozen Cold War-era sites nationally that could be eligible for National Historic Landmark status, grouping it with its sister bunker on Peanut Island near Kennedy's Palm Beach retreat. Nantucket Preservation Trust executive director Mary Bergman called the possibility a reminder that the island's history runs well past the whaling era. Whether that designation ever comes through, the bunker's entrance, a rust-streaked semicircular hatch rising out of the grass, remains one of the stranger landmarks a Tom Nevers resident can point out to a visitor without having to explain much else.

Why the Field Carries This Much Weight

Most Nantucket neighborhoods organize their week around a beach, a market, or a strip of restaurants close enough to walk to. Tom Nevers has none of that. Its beach is quiet and often foggy, its homes sit on acreage rather than blocks, and the nearest commercial activity requires a drive up Milestone Road toward town or Sconset. What the neighborhood does have is 22 acres of shared grass that somehow supports a decade-old softball tradition, a newly revived baseball league with more than 75 members, a September fair drawing visitors from across the island, and a piece of presidential Cold War history, all without any of it crowding out the rest.

That is not a small thing for a neighborhood built around privacy and distance. It means the closest thing Tom Nevers has to a town square was never a square at all. It was a ballfield that almost went to seed, brought back one Facebook post at a time.

If you are curious what a season at Tom Nevers Field actually looks like from the inside, or want to talk through what a property near it might mean for your own routine, Jeremy Morgado is happy to walk through it with you.