15 Enchanting Things to Do in Roxbury NY (Weekend Getaway Guide)

The Roxbury at Stratton Falls in Roxbury New York at dusk

Looking for all the amazing things to do in Roxbury, NY? You’ve come to the right place! This charming town nestled in the heart of the Catskills makes an unbelievable getaway. We went for my birthday in the fall and it was just absolutely breathtaking.

Not only do you have all the unique things to do in the Catskills region at your doorstep here, but you also have plenty of charming towns in the Catskills nearby you can visit, which are some of the best towns in New York to pay a visit to.

Not to mention, Roxbury is home to one of the most unique stays in the country! Which is why this is one of our favorite romantic getaways in Upstate New York!

Renowned for its picturesque landscapes, charming small-town atmosphere, and vibrant arts scene. Visitors are drawn to Roxbury’s scenic beauty, with opportunities for outdoor adventures like hiking, skiing, and fishing.

The also town boasts historic architecture, including the iconic Jay Gould Memorial Church, reflecting its rich heritage and ties to Gould himself who was born here, a railroad magnate and robber baron of the Gilded Age. You can actually visit his incredible Gilded Age Mansion, Lyndhurst in Tarrytown too, one of our favorite things to do in the Hudson Valley (and easy addition to your getaway to Roxbury coming from NYC if you want to make a stop in the Hudson Valley before continuing through the Catskills region).

So without further ado, see why we loved our weekend getaway in Roxbury and all the wonderful things to do here.

Disclaimer: This post contains affiliate links.

What to do in the Town of Roxbury, NY

Stay at the Roxbury at Stratton Falls

the upstairs bedroom at Cinderella's Gown at the Roxbury Experience in Roxbury New York

One of our bucket list things to do in Roxbury, NY was staying at the Roxbury Motel specifically at the themed cottages at the Roxbury at Stratton Falls, and we finally got to check this one off! If you’re looking for unique and luxurious accommodation in Roxbury, this is the place.

The boutique hotel is owned by husbands and business partners, Gregory Henderson and Joseph Masa. It’s located on 27 acres of wooded land and features 8 suites and 7 cottages, each with its own private entrance and outdoor hot tub. But the big appeal of staying at the Roxbury at Stratton Falls is the fabulous themes of each room.

Henderson and Masa are NYC transplants with a passion for the theater, and they’ve used that flare for the dramatic to transform the elegant mansion inn. They’ve trimmed it out with bespoke décor and elaborate themes that make each stay a special and unforgettable experience!

You can enjoy a stay in the stunning mansion, with sprawling suites that feature charming and graceful themes based on local legend and history. Or stay in the magical tower cottages, with more whimsical themes like Cinderella’s Dress and Dracula’s Fangs.

Draculas Fangs living room at The Roxbury at Stratton Falls in Roxbury NY

Imagine waking up next to a giant pumpkin carriage or feel like you’re living in Dracula’s lair! If I had to pick a favorite, I couldn’t both rooms we stayed in were so unique and so memorable in their own way.

Each of the cottages we stayed in had so many intricate attention to detail that went into every corner of the space. It was rather impressive! And since my birthday is around Halloween, this felt like the perfect place to have a getaway!

Stratton Falls on site at the Roxbury Motel in Roxbury NY in the Catskills

When you stay at the Roxbury at Stratton Falls, you can also enjoy the property’s top-notch amenities. They include a swimming pool, pond, gorgeous hiking trails, gardens, oh and a private waterfall!

You can book a room or cottage here if not at the very least look at all the different themes they have! This is THE place to base yourself while exploring all the best things to do in Roxbury!

Explore Downtown Roxbury

interior of The Fierce Grizzly restaurant in Roxbury NY

The Main Street Historic District of the town of Roxbury, NY is a charming stretch of road lined with colorful storefronts and beautiful Catskill mountain views. You’ll also find quite a few sites on the National Register of Historic Places, like the First Old School Baptist Church of Roxbury which dates back all the way to the 1850s!

There are local shops to explore, like the Roxbury General that’s always good for a gift, souvenir, or bite to eat. They have alot of local pantry and grocery items that are fun to browse and it’s really the only real grocery option around.

And if you get hungry, we recommend stopping into The Fierce Grizzly. You’ll love the beautiful setting, cozy ambiance, and timeless cuisine (including a great wine list!). I adored the vibe in here.

Or for a truly special meal, head down Bridge Street for The Old Mill. This restaurant and bar is where to come for an experience and impeccable service in a historic setting.

Really, Downtown Roxbury, New York offers guests the perfect blend of sleepy small town, historic charm, and one-of-a-kind experiences.

Jay Gould Memorial Church

Just a 3-hour drive from New York City, Roxbury might interest those with a fascination for Gilded Age-era landmarks. Jay Gould was a renowned railroad magnate of the time with deep roots in New York City. He had connections to Tammany Hall and is known for purchasing the gorgeous Lyndhurst Mansion, one of the most famous Gilded Age mansions in New York. But before that, Jay Gould was born and raised in the town of Roxbury, NY!

One of the oldest churches in the area, the Reformed Church of Roxbury, was founded in the early 1800s when the congregation met in a barn. After several failed attempts to fundraise for a building, Gould committed to funding a stone structure for the church.

In 1894, the Jay Gould Memorial Church was opened. Today, you can see the classic Gothic-style stone structure as you drive along historic Main Street. You can attend one of the church’s regular services to see the 3 beautiful stained-glass windows. And while you’re here, take time to head around back to visit the tranquil Kirkside Park.

Kirkside Park

Visiting Kirkside Park is one of the best things to do in Roxbury, NY, especially if you love history and the great outdoors. That’s because Kirkside Park is so much more than just a local park!

The land was once part of the estate of Helen Gould Shepard, daughter of railroad magnate and Roxbury-born, Jay Gould. When you visit the adjacent Jay Gould Memorial Church, you’ll see the historic Kirkside farmhouse built in 1857.

Shephard actually purchased the 14 acres of land and the farmhouse in 1904, after the church dedicated to her father was built. She added the iconic Adirondack-style footbridges that take you across the East Branch of the Delaware River as it winds through the park. And while the land and farmhouse changed hands over the years, it was officially saved as a public park in the 1980s.

Today, you can visit this small and beautiful local park in Roxbury by driving down Kirkside Driveway. Enjoy this small piece of local history as you enjoy a picnic, with picnic tables under shade trees. Or take the kids to the playground if they’re in tow.

You can also simply explore the property, taking in the river and historic structures throughout the park. During the summer, Kirkside Park is also the location of many casual local events.

The Roxbury Arts Group

Heading further south on Main Street, turn left on Vega Mountain Road and you’ll see the gorgeous building that houses the Roxbury Arts Center. The Roxbury Arts Group has a few locations throughout Delaware County, and this one in Roxbury is an essential stop for art lovers of all shapes and sizes.

On any given day, you’ll find a variety of things happening at the Roxbury Arts Center. This community center often hosts local artists through rotating exhibits. You can check out their calendar to find out about upcoming performances or attend a workshop.

Local to the area and interested in meeting like-minded people? The center also hosts free RPG nights with games like Dungeons & Dragons and Magic: The Gathering!

The Roxbury Arts Group is all about making the arts an accessible part of everyday life for all ages. While you’re looking for things to do in Roxbury, NY, don’t hesitate to check out what’s going on here!

Hit the Slopes at Plattekill Mountain


A popular Catskills winter getaway attraction that draws visitors to Roxbury, New York (and some of the best skiing near NYC) can be found at Plattekill Mountain.

This small, old-school ski mountain is perfect for snowboarders and skiers of all skill levels. Plattekill boasts just 4 lifts and 38 different trails, but they include everything from bunny slopes for beginners to black diamonds for experienced skiers. 

I am a beginner snowboarder and found this mountain to be a bit challenging! The trail I went down was narrower than I’m used to (I need space to carve because I really am a rookie) and through the forest. It was a beautiful trail, but if you have the issue I have and need a wide-open run, that’s something to consider!

Not a skier? You can try the mountain’s other winter activities, like snow tubing lanes, snowshoeing, or cross-country skiing. Plus, Plattekill Mountain is well-known for being family-friendly, offering programs that make the trails accessible to kids and new skiers alike. You can check out both private and group lessons that are available for an impressive range of ages.

Warm up and grab a bite at the classic après ski bar, or just enjoy the laid-back atmosphere of the resort by visiting the lodge. If you need gear, there’s a rental shop on site with the essentials. And, yes, Plattekill Mountain is pretty basic, but that’s part of its old-school charm! It’s one of the last locally owned ski areas on the East Coast.

In the warmer months, Plattekill transforms into a hiking and mountain biking destination, with an extensive trail network. Also, they don’t offer lodging on the mountain, but you’re a quick drive from Roxbury. Or make it a day trip by booking one of Urban Sherpa Travel’s shuttle packages from Manhattan during the winter season.

Take a Scenic Train Ride

Delaware-&-Ulster-Railroad in-Arkville-New-York-near-Roxbury-in-the-Catskills

The Delaware & Ulster Railroad offers scenic train rides that depart from Arkville, a short drive from Roxbury. The area saw its heyday for a short time in the early 1900s, when the railroad brought prosperity to the area. Today, you can ride this vintage train ride through the scenic Catskill Mountains and along the Delaware River.

From Arkville, you’ll enjoy a round-trip ride on a historic locomotive. Throughout the year, a variety of different rides are offered, including fall foliage rides, kid-specific event rides, and popular seasonally-themed rides. During the summer, adults will love the Twilight on the Rails rides that feature live music, wine tastings, and a picnic meal in an air-conditioned car.

In the fall, one of the best things to do in Roxbury, NY is the ever-popular Train Robbery ride! It takes you back in time with actors in period costumes that immerse you in a live-action train robbery. And during the weekends in December, everyone will love riding the Silver Sleigh Flyer, where they can enjoy snowy views, hot cocoa, and visits with Santa!

Most train rides are round trips from Arkville and last about 2 ½ hours. Along the way, you’ll be treated to breathtaking views of the surrounding countryside. Depending on the time of year and the train you’re on, you can book an open-air car or an enclosed coach car with air conditioning.

And while you’re visiting the Delaware & Ulster Railroad, make sure to plan a little time at either the Roxbury or Arkville depot stations. Both double as museums showcasing the railroad’s heritage. Outside the Arkville depot, you can also check out retired vintage trains.

Note: While the Delaware & Ulster Railroad has been closed since 2022 for track repairs, it’s slated to reopen soon so check before planning your visit!

Catskill Scenic Trail


Outdoor lovers seeking a day of hiking will want to embark on the Catskill Scenic Trail, which has a branch that reaches just north of the town of Roxbury, NY. This scenic trail is now 26 miles in length, running from Bloomville, up to Stamford, across to Grand Gorge, and then down to Roxbury. Hikers can enjoy a variety of landscapes along the way, from dense woodlands to open meadows.

The gravel and dirt trail is relatively flat and level, making it a great option for all skill levels, from seasoned hikers to casual strollers. Plus, the Catskill Scenic Trail is open all year round, offering you a chance for a range of experiences. You can also try biking, horseback riding, or jogging during the warmer months, or cross-country skiing in the wintertime.

The Catskill Scenic Trail is popular in the summer for its lush scenery and in the fall, as you pass through several farms and open valleys offering stunning fall foliage. The trail is also pet-friendly (as long as they’re leashed) and popular with families. And for those seeking a more challenging trek, offshoot trails lead to elevated viewpoints, rewarding you with panoramic views of the Catskill Mountains.

There are different trailheads and places to park along the 26-mile route. Assuming you’re starting at the trailhead on the Roxbury side, head to Route 30, where it meets Hardscrabble Road. There’s a parking lot here, and you’ll see the well-maintained path just off the lot.

Go Kayaking

Lake Wawaka

For an absolutely charming way to spend a few hours outdoors during the summer, consider kayaking at Susan’s Pleasant Pheasant Farm! This is one of the most unique and fun things to do in Roxbury, NY.

The farm is a casual, family-owned spot that opens its doors to visitors as soon as spring arrives through the end of the summer. And though kayaking is seasonal, the farm is home to a bed & breakfast and crystal shop that you can visit year-round.

When you arrive, you’ll probably be greeted by the husband and wife who run the property. They’ll assist you in choosing a canoe or paddle board and give you the run-down of what else is available to you on the property. They’re usually open Wednesday through Sunday from 10 AM to 5 PM, but staff will go home early if no one is there by closing time. It’s just that kind of place!

Spend a few hours kayaking or paddle boarding along the 1-mile lake that runs through the property. Ready to get off the water? While you’re at Susan’s Pleasant Pheasant Farm, spend some time walking the lush grounds, peeping local wildlife, or enjoying a picnic.

There’s disc golf and a swimming hole. And keep an eye out for dates for the annual Pheasant Fest in early September! This one-day event will include live music, kayak races, disc golf, delicious food, and more.

Antique Shopping

There’s just something magical about antique shopping in the Catskills. It’s the perfect place to find those special pieces without the high price tag you might find in Brooklyn!

And while you’re exploring sleepy Roxbury, New York on the weekends, you won’t want to miss a chance to stop by Antiques at Rick’s Barn, just off NY-30, south of downtown Roxbury.

While this is the only place we found in the town of Roxbury to go antique shopping, it’s worth the stop. Only open between 10 AM and 5 PM on the weekends, you can be one of the few who get to peruse the curated collection of quality antique furniture and rugs. Rick will work with you concerning any special pieces you may be looking for.

Visit the Woodchuck Lodge of John Burroughs

Historic Photo of Dr. Clara Barrus at Woodchuck Lodge / Editorial credit: Everett Collection / Shutterstock

For history lovers looking for special things to do in Roxbury, NY, look no further than the Woodchuck Lodge of John Burroughs! This historical sight off Hard Scrabble Road offers a glimpse into the life and philosophy of John Burroughs, a prominent figure in American literature and environmentalism.

Burroughs spent many summers in the early 1900s at Woodchuck Lodge, a farmhouse that dates back to the 1860s. He found inspiration for his writing in the rugged and wild charm of the Catskill Mountains. Today, the lodge and surrounding property are on the National Registry of Historic Places and are run by the New York Parks Department.

When you visit, you’ll get to see the farmhouse where Burroughs spent his summer between 1910 and 1920. The lodge itself is a time capsule, preserving Burroughs’s simple but elegant lifestyle. You’ll feel like you’re stepping back in time as you observe the writer’s original furnishings, personal artifacts, and extensive library.

Nature enthusiasts can explore the picturesque trails around Woodchuck Lodge, known as Slabsides. These trails wind through the gorgeous and peaceful landscape that captivated Burroughs. You’ll soon see why this was the setting that gave him such an appreciation of the natural world!

Throughout the year, Woodchuck Lodge hosts events and programs that celebrate Burroughs’ legacy, from literary discussions to nature walks. It’s a place where you can connect with the wisdom of a man who advocated for preserving the environment and finding solace in the beauty of the outdoors.

Check Out Margaretville


Less than 15 miles south of Roxbury, New York, is another must-visit town that’s a natural stop when you’re exploring the area. With foundations that date back to the 1700s. But the town really got its boom when the Delaware Railroad came to town in the 1900s and has some interesting claims to fame.

Margaretville was the hometown of Dr. Orvan Hess, who invented the fetal heart monitor. He was also one of the first doctors to treat someone successfully with penicillin. Today, Margaretville largely gets its traffic from tourism, boasting an adorable population of less than 600!

You’ll start your journey by strolling through the downtown area, which is centered around a 1000-foot-long stretch of Main Street. This is where you’ll discover a feast for the eyes, with brightly painted storefronts, historic structures, ancient and crumbling homes, and the Delaware River winding through it all!

All along Main Street, you can check out a variety of shops, from boutique clothing and thrift stores to adorable gift shops and art galleries. Margaretville’s shopping scene caters to all tastes.

When it’s time to refuel, make your way to Locale Trattoria. This Italian eatery combines a cozy ambiance with outstanding dishes, offering a menu that highlights fresh, locally sourced ingredients.

Then, if you want to get outdoors and enjoy the Catskills scenery, Margaretville offers access to nearby hiking trails. They offer the perfect blend of nature and small-town charm.

The Ark Bowl & BBQ

The Ark Bowl & BBQ in Arkville New York

Across from Locale Trattoria is the perfect post-dinner game (or another meal option if you’re in the mood for something more casual). The Ark Bowl & BBQ is a great vintage bowling alley in Margaretville that you have to see!

It’s a great spot for couples, singles, and families alike, offering a night of bowling in a timeless, vintage bowling alley. I love how retro everything was inside of here. The bowling alley feels straight out of the 1960s, complete with 8 classic lanes and a chill atmosphere. It’s the perfect setting for a casual night out with friends or a fun family outing.

The onsite Smokehouse at The Ark Bowl serves up a yummy selection of smoked meats, from tender pulled pork to savory brisket. The aroma of slow-cooked goodness fills the air, preparing you for a satisfying dining experience!

The Ark Bowl & BBQ is also a bit of a community hub, and regularly hosts events throughout the year, including local races, musical performances, and more. Check their events calendar for the latest updates.

Pakatakan Farmers Market


And if you’re spending a Saturday morning exploring the NY-30 between Margaretville and Roxbury, plan a stop at the Pakatakan Farmers Market. One of the top things to do in Roxbury, NY, the Pakatakan Farmers Market is a local treasure trove if you’re looking for a taste of the region’s fresh, locally sourced products.

Open seasonally (typically from mid-May through October) this bustling and charming market brings together farmers, artisans, and community members. Strolling through the market, you’ll encounter a diverse array of stalls showcasing all kinds of goods.

From colorful fruits and vegetables to artisanal cheeses, baked goods, and handcrafted items, the Pakatakan Farmers Market offers it all. And while you peruse vendors, you can enjoy live music.

But what makes Pakatakan Farmers Market so memorable is not just the variety but also the sense of community. You can come here to hear farmers share stories, talk to artisans about their craft, and connect with locals. The market also supports local causes, which just adds to its feel-good charm.

Things to Do Near the Town of Roxbury, NY

While you’re looking for things to do in Roxbury, NY, we highly recommend these destinations. Since you’re in the area, they’re definitely worth the drive!

Gilboa Fossils

Gilboa Fossils, about 10 miles north of Roxbury, is perfect for anyone who has ever found fossils fascinating! At this fossil museum, you’ll step back around almost 400 million years. The site is a significant spot because it’s home to the world’s oldest forest remains.

At the fossil museum, you’ll find the Gilboa stumps – the fossilized remains of ancient trees that once dominated the landscape. These fossils are like a window into the past, providing insight into the evolution of life on Earth. There’s also a guided trail, the Fossil Forest Trail, where you can learn about the significance of the fossils and the geological history of the region.

For those with a passion for paleontology or a simple curiosity about Earth’s prehistoric past, Gilboa Fossils is fascinating. Check them out from late May through the beginning of October. They’re usually open on the weekends from noon to 4 PM.

Windham Path

The covered bridge at the Wyndham Path in the Catskills NY in the fall

If you need to stretch your legs on your way back to NYC from Roxbury, New York, we recommend planning a pit stop at Windham Path! It’s a laid-back outdoor spot with an easy nature trail that’s great for everyone, whether you’re a hardcore hiker or just want a relaxed walk.

The 1.5-mile loop path winds through emerald, green meadows and woods, so you can soak up a peaceful nature experience. The trail is well-kept and open all year, so you can check it out in any season. Windham Path is also popular with area birdwatching. And with benches along the way, you can take a break, enjoy the view, and take in the outdoors.

Where to Stay in Roxbury, NY

The Cottage Towers at the Roxbury at Stratton Falls at dusk in Catskills NY

Is the choice not obvious enough for you? You absolutely need to plan your entire weekend or getaway in the Catskills around The Roxbury Motel! This is without a doubt one of the most unique places to stay in the Catskills and state of New York.

The hardest part will be choosing which room you want to stay in! What’s important to know is that there are two different properties associated with The Roxbury Motel.

The Roxbury Motel is located in downtown Roxbury and their very first property. This is more of a motel with themed rooms you can stay in.

The rooms here are heavily influenced and inspired by the TV shows and films of the 1960s and 1970s. This is where you’ll find more contemporary (think mid-century contemporary) rooms and a few fun themes like The Wizards Emeralds, a Wizard of Oz themed stay!

The second property is The Roxbury at Stratton Falls, this is located a few miles down the road and just outside of the town of Roxbury.

This property has the historic Italianate mansion from 1848 that was built on this land because of the gorgeous Stratton Falls that are here, which you can hike down to and enjoy the different viewing areas and sitting areas overlooking the falls during your stay (Roxbury Motel guests have the option to come here too).

In 1790, Revolutionary War soldiers Joseph and Samuel Stratton journeyed to New York State from Connecticut to start anew after surviving the burning of Fairfield. They discovered a pristine site with a powerful waterfall, known as Stratton Falls, where they built a woolen mill. This area became the first settlement of Roxbury, inspiring the themes of the resort’s mansion rooms.

So you also have the option to stay in one of the rooms in the historic inn or at the same property is where you can find the whimsical-themed Tower Cottages (pictured above). This is where you’re going to find the themed rooms we stayed in, Dracula’s Fangs and Cinderella’s Gown.

In addition to serene walking trails to Stratton Falls, this property also houses the pool and spa at the Crooked Cabana. The swimming pool is seasonal and the spa features a dry sauna and hot tub open year-round. They require you to schedule a time to visit these facilities, so be sure to plan that upon your visit.

This truly is a one-of-a-kind experience and we hope that you can book and experience a stay at the Roxbury Motel during your Catskills getaway! We were HUGE fans and would love to go back and stay in different themed rooms!

Enjoyed this guide for what to see and what to do in Roxbury, New York? Bookmark this Catskills travel guide for later and be sure to share the love on Pinterest below!