The Roxbury, NY Guide: A Tiny Catskills Town With a Very Big Imagination
- JoJo Wanders Official
- Aug 4, 2021
- 7 min read
Updated: Jul 31
Roxbury is the sort of town that makes you check the population twice.
The hamlet is quiet. Historic buildings line the streets. A public park stretches behind a stone church, the mountains rise around the valley, and at first glance the whole place seems far too well behaved to be hiding anything dramatic.
Then you find the hotel rooms that look like someone gave a Broadway set designer a key card and no adult supervision.
A few blocks away, an arts center fills a century-old building with performances and exhibitions. Outside town, an independent ski mountain keeps doing things its own way. The public golf course began as part of a Gilded Age estate. The grocery store occupies an 1840 corner building and looks as carefully considered as places in towns ten times the size.
That is Roxbury’s trick. It never stops being small. It simply refuses to think small.
Before visiting, understand that Roxbury means two different things. There is the walkable hamlet, where Main Street, Kirkside Park, restaurants, shops and the arts center sit close together. Then there is the wider Town of Roxbury, which includes Grand Gorge and Denver and spreads into the surrounding Catskills. Several well-known stops require a car.
Why Roxbury Feels Different
Roxbury rewards people who notice details. The Main Street historic district is layered with Greek Revival, Victorian and civic architecture. Kirkside Park was once part of Helen Gould Shepard’s estate. The Roxbury Arts Center occupies a 1911 building she commissioned. Shephard Hills Golf Club also traces its beginnings to the Gould family property.
The town’s history is not sealed behind velvet ropes. It is still being used. You can walk through old estate grounds, attend a performance in a historic building, buy groceries in a nineteenth-century storefront and then sleep in a room designed during what appears to have been a very glamorous fever dream.
Most towns choose between preservation and reinvention. Roxbury seems to have asked why it could not have both.
Where to Stay
The Roxbury Village Side and Stratton Falls
The Roxbury is not merely the best-known hotel in town. It is part of the town’s personality.
The Village Side sits near the hamlet’s walkable core. Stratton Falls is a separate property with more space, dramatic accommodations, its own grounds and a private trail to the waterfall. Guests can use shared amenities that include breakfast, lounges, fire pits, Wi-Fi, a seasonal pool and spa facilities.
The room designs are unapologetically theatrical. Depending on the room, you may feel as though you have entered a fairy tale, film set, archaeological fantasy or the private quarters of someone who won the lottery and immediately called an interior designer with excellent boundary issues.
Roxbury has plenty of historic restraint outside. The hotel is where the town lets the sequins out.
Choose the Village Side when being near Main Street matters. Choose Stratton Falls when the room, grounds and waterfall are meant to be a larger part of the getaway. The properties are pet-free, so travelers with animals will need another lodging plan.
Where to Eat, Drink and Stock the Car
Roxbury’s food scene is not enormous, which makes accuracy more important. A closed kitchen or misunderstood schedule can rearrange an entire evening when the next option may be several miles away.
Chappie’s
Chappie’s is one of the strongest anchors for a proper meal in the hamlet. It sits on Main Street, accepts reservations and operates seven days a week, although hours vary and should be confirmed before visiting.
Build an evening around it rather than treating dinner as an afterthought. Roxbury is not known for nightlife that begins at midnight. Its better evenings tend to unfold slowly and end at a civilized hour.
Watershed
Watershed is the daytime counterpoint to Chappie’s. It serves coffee, breakfast and lunch and describes itself as Roxbury’s front porch.
The phrase works because Watershed feels less like a stop on an itinerary and more like the place where the itinerary begins to loosen. You arrive for coffee, hear what is happening in town, notice who keeps walking in and understand that the café is performing at least three jobs at once. Seasonal hours can change, so check before making it the first immovable point of the morning.
Good Grocer
Good Grocer occupies a historic corner-store building dating to 1840 and sells groceries, produce, prepared foods, local products, beer and cider.
It is practical, but not merely practical. You go in for sparkling water and emerge with cheese, bread, cider and an unrealistic belief that you will prepare a tasteful picnic before sunset. Travelers staying without full restaurant plans should stop early. “We will figure out dinner later” has ended many romantic weekends with crackers eaten over a bathroom sink.
The Old Mill remains part of Roxbury’s food story, but its official site currently notes a temporary closure for mechanical repairs. It should return to a current recommendation list only after the business publicly confirms that it has reopened.
Roxbury’s Walkable Core
Kirkside Park
Kirkside Park is where Roxbury stops performing and simply breathes.
The 14-acre public park was once part of Helen Gould Shepard’s estate. Today it includes paths, bridges, riverfront green space and a multi-use barn pavilion behind the Jay Gould Memorial Reformed Church.
This is not a park you need to conquer. You do not need technical shoes or a hydration strategy involving multiple powders. Walk until the town feels quieter. Sit near the water. Let the trip become less efficient. Roxbury is not improved by speed.
Historic Main Street
Roxbury’s Main Street and surrounding hamlet are listed on the State and National Registers of Historic Places. Printed walking-tour brochures are available at locations including Town Hall, the library, the hotel and the arts center.
Without context, the district is a handsome collection of old buildings. With context, it becomes a story about wealth, philanthropy, architecture, civic ambition and the long afterlife of the Gould family. The town preserved these buildings without turning them into a silent museum. Many remain active parts of daily life.
Arts and Culture
Roxbury Arts Group
The Roxbury Arts Group makes it clear that the town’s creative energy is not confined to one eccentric hotel. The organization presents year-round performances, exhibitions, workshops and classes at the Roxbury Arts Center and other Delaware County venues.
Check the current calendar before planning the trip. A concert, performance or exhibition can become the reason the weekend holds together. Without an event, you may visit several good places. With one, the town begins to feel as though it invited you for something specific.
Liberal Arts Roxbury
Liberal Arts Roxbury adds another contemporary layer to Main Street. The gallery and multimedia exhibition space occupies a historic corner-store building with its own Gould-family connection. Hours can be limited, so verify them before treating it as a guaranteed stop. Small-town arts schedules often make perfect sense to the people operating them and absolutely no sense to someone arriving at 2:17 p.m. on a Tuesday.
Outdoors and Recreation
Plattekill Mountain
Plattekill is one of the remaining independent ski mountains in the Catskills, and that independence is part of the appeal. In winter, skiing, snowboarding and tubing are the clearest reasons to go. The summer calendar is more limited, so look for a specific event or operating notice before driving out.
Plattekill fits Roxbury because it shares the town’s personality: small, self-directed and not especially interested in becoming a generic version of somewhere else.
Shephard Hills Golf Club
Shephard Hills is a public nine-hole course with alternate tees that create an 18-hole experience. It includes a driving range, rental clubs, clubhouse and seasonal restaurant.
The history is the more surprising part. The course began as part of Helen Gould Shepard’s estate, and the clubhouse occupies an old stone guesthouse. Even here, recreation comes with a backstory.
A Simple One-Day Plan
Begin at Watershed with coffee or breakfast, then walk Main Street before the day becomes complicated. Pick up a historic walking-tour brochure and continue through Kirkside Park, where the town’s grand history becomes a public place rather than a paragraph on a plaque.
Stop at Good Grocer before leaving the walkable core. This is partly for the building and local products and partly because future you may be grateful for snacks.
Choose one afternoon anchor. In winter, make it Plattekill. In warmer weather, book golf at Shephard Hills, follow a scenic drive through the wider town or stay in the hamlet for an exhibition, arts event and longer park walk. Return for dinner at Chappie’s or time the evening around a Roxbury Arts Group performance.
The mistake would be trying to fit every section of this guide into one day. Roxbury is tiny, but it is not a checklist.
A Two-Night Weekend
Friday: Arrive, settle into the hotel and let the room be part of the entertainment. Walk Main Street if daylight allows, then keep dinner simple.
Saturday: Start at Watershed, explore the historic district and Kirkside Park, visit Good Grocer and add one cultural stop. Spend the afternoon at Plattekill, Shephard Hills or another seasonal activity. End with dinner at Chappie’s or a performance.
Sunday: Give the hotel grounds time rather than treating checkout as an emergency evacuation. Guests at Stratton Falls should walk the private trail when conditions allow. Then take a scenic drive through the wider Town of Roxbury before heading home.
The Bottom Line
Roxbury is not large, but it has an unusually strong sense of itself. The town preserved its architecture without embalming it. It kept its public spaces useful. It allowed serious art, eccentric design, local food and independent recreation to grow beside its history without requiring everything to match.
Come for the hotel, the park, the mountain or the Gould history. Stay because a town this small should not have this many layers, and somehow does.
