Most towns get shaped by what came through them. Chaplin got shaped by what went around it. When the state straightened Route 198 in 1929, the old north-south road curved off into a mile-long cutoff and stayed there, and the village center along it stopped changing.
That single piece of road engineering is the thread running through almost everything worth doing here on a weekend. The Federal-era houses on Chaplin Street, the quiet at Diana's Pool, the newly linked preserves on the town's edges — they exist in their current form because the traffic, the industry, and the tourists mostly went elsewhere.
The Village Route 198 Bypassed
Walk Chaplin Street on a Sunday morning and you are walking through a compressed thirty-year building boom. Between 1820 and 1850, roughly 25 homes, a tavern, a general store, a dry goods store and a merchant's store were built adjacent to the church along a curved portion of the major north-south route that paralleled the Natchaug River, so the majority of the houses that line the village street were built within a single thirty-year period.
The anchor is the 1812–15 Congregational Church, which stands on a knoll overlooking the street. Almost every other building on the street came within a generation of it.
Then the road moved. Chaplin Street became a mile-long cutoff when State Route 198 was straightened in 1929, leaving most of the village homes intact, and in July 1974 Chaplin Village was designated a Historic District to preserve the character of the buildings and their settings. The National Register followed in 1978.
For residents, the practical result is that a slow walk from the top of the knoll down to number 46 (a general store erected c. 1828, most likely by Isaac Goodell) is one of the few places in northeastern Connecticut where you are looking at a village in something close to its original massing. If you own an older home in town and are trying to figure out what a period-correct paint scheme or window profile looks like, the answers are on this street.
One thing to know if you own inside the district: the Historic District Commission still meets in the Chaplin Library conference room, and its 2026 meeting dates are 2/10, 5/5, 9/8, and 11/10. Any exterior work visible from a public way needs to go through them.
The Pool With the Parking Problem
Diana's Pool is the one spot in Chaplin that everyone from outside town has heard of. If you live here, you already know the drill, but the specifics are worth being honest about.
The trailhead sits off Diana's Pool Road just after the turn from Route 198. Coming from the intersection of Route 6 and Route 198, you head north on Route 198 for approximately 0.5 miles, pass the Chaplin Firehouse on your right, turn right onto Diana's Pool Road, and a small parking lot immediately on your left accommodates approximately 6 to 7 vehicles. That is the entire lot. There is no overflow.
Cars parked on the side of the road get ticketed, and a cruiser reportedly drives by roughly every hour. That is why locals do the pool on a Tuesday evening or before 9 a.m. on a Saturday, and not at noon in July.
The walk itself is short. Diana's Pool is an easy hike that covers 1.3 miles with an elevation gain of 49 feet, taking about a half hour to an hour to complete. The payoff is the large scenic swimming area with an S-shaped, triple-tiered waterfall on the Natchaug River. Swimming is officially prohibited. Fishing for trout and sitting on the slanted boulders is not.
One historical footnote worth carrying with you: just north of the main pool, there are large stone blocks that, according to historical maps from the mid-1800s, may be the ruins of the Natchaug Paper Co. If you have kids who need a reason to keep walking past the first set of rocks, that is your reason.
A Preserve Most Residents Haven't Walked Yet
Tower Hill Preserve is the newest addition to Chaplin's outdoor inventory, and a lot of people who have lived here for years still haven't been on it.
The preserve spans 236 acres at 513 Phoenixville Road and was a gift from the Alexander Family Trust in 2021. It is a crucial link for wildlife, connecting the areas between Mansfield Hollow State Park and Natchaug Forest. That corridor function is the interesting part. It is not a stand-alone park so much as the missing middle piece between two much larger tracts.
On the ground, you get stone walls, the foundation of an old house, and quiet woods. The land was once part of Benjamin Chaplin's holdings in the late 18th century, and remnants include stone walls built in the 1800s and the foundation of one of the first houses with indoor plumbing in Chaplin.
For a resident with a dog and an hour, this is currently the least crowded option in town.
The Quiet Ones
Chaplin has a cluster of small preserves and neighboring sanctuaries that fall into what you might call the "no one there on a Wednesday" category. Here is how they compare on paper.
| Property | Size | What it's for |
|---|---|---|
| Hubbard Sanctuary | ~38 acres in Chaplin | Walking trails, part of Joshua's Trust |
| Tower Hill Preserve | 236 acres | Wildlife corridor, historical remnants |
| James L. Goodwin State Forest | ~2,000 acres in Hampton | 14 miles of multi-use trails, Pine Acres Lake |
| Trail Wood | 168 acres in Hampton | Literary sanctuary, roughly 4 miles of unblazed trails |
Hubbard Sanctuary is worth knowing because of who gave it. The Hubbard family moved to the house and farm from New Britain in 1938, and Mary MacNaughton Hubbard, called Mollie, lived there until 1987. A scientific illustrator and academic advisor in the Biology Department at the University of Connecticut, she donated 38 acres in Chaplin to Joshua's Trust in 1985, land now known as Hubbard Sanctuary. She also donated land to the Town of Chaplin for its town offices and Edward Garrison Park. Much of what you use in daily civic life in town sits on land she gave away.
Just over the line in Hampton, the James L. Goodwin State Forest is close enough that most Chaplin residents treat it as a home trail. Fourteen miles of trails, including an equestrian trail and the Air Line Trail, the 135-acre Pine Acres Lake, three large ponds, native plant wildlife gardens, and the Goodwin Conservation Center combine to make this State Forest an eastern Connecticut treasure. The Conservation Center runs programs year-round out of the white farmhouse at 23 Potter Road in Hampton; for information or to register, visit ctparks.com/events.
Trail Wood is the other Hampton neighbor. It was the home of naturalist Edwin Way Teale, and over his career Edwin wrote 27 original books on natural history, science, and photography, and ten were completed here, including Wandering Through Winter, which earned the 1966 Pulitzer Prize. The sanctuary is 168 acres with nearly four miles of trails featuring old farm fields, forests, brooks, and ponds, and highlights include Teale's brushpile study, Writing Cabin, insect garden with a sundial, Nellie's Summerhouse with views of Hidden Pond, and beaver pond observation areas.
One useful detail if you have a friend visiting who does not hike: to preserve the landscape as the Teales would have experienced it, the trails are not blazed, so download or take a trail map from the information shed and use the kiosks at key intersections for guidance.
When to Show Up at Chaplin Farms
Pick-your-own is the one thing in Chaplin that has a real calendar. Chaplin Farms is at 860-455-7683, offers pick-your-own peaches, apples, pumpkins, and Christmas trees, is open daily 10 to 6 June through December, and grows over 15 apple varieties including Macoun and Mutsu.
The practical read on that calendar for a resident:
- June and early July: strawberries at farms across the region, peaches beginning
- August: peach season proper, which is the reason to go if you have never been
- September and October: apples, with Macoun coming in mid-September and Mutsu later
- November and December: Christmas trees
Peach season is the one that catches people. If you have only ever picked apples in Chaplin, you are missing the softer, messier month.
A Sunday That Uses All of It
Here is the residents' version, ordered to avoid the parking problem and the crowds.
- 8:00 a.m. — Coffee at home, then Diana's Pool while the lot is empty. Walk past the main pool to the old paper company ruins.
- 10:00 a.m. — Drive five minutes to Chaplin Street. Park near the church, walk the district end to end, look at door casings.
- 11:15 a.m. — Chaplin Farms for whatever is in season. Call ahead in shoulder weeks.
- 12:30 p.m. — Lunch at home or a packed lunch to the next stop.
- 1:30 p.m. — Tower Hill Preserve or Hubbard Sanctuary if you want quiet, Goodwin if you want distance.
- Late afternoon — Trail Wood for a shorter, contemplative loop. Check the Connecticut Audubon calendar for any open programs.
You will not see another Chaplin resident at most of these stops. That is the point.
Why This Matters If You Own an Older Home Here
The 1929 road change did more than preserve a historic district. It kept Chaplin off the corridors where speculative development took over other Windham County towns in the late 20th century, which is why the housing stock skews toward pre-1950 wood-frame homes with the maintenance profile that comes with them. If you are working through an older home in town and trying to figure out whether a project is worth doing before you list, or whether a house you are considering has quirks that are normal for the era, the answers are usually specific to this kind of village fabric.
When you are ready to talk through what your Chaplin home is worth in today's market, or what to look for in one you are considering, reach out to Lindsey Niarhakos. Let's connect.
