3 Days In Roxbury NY: An Epic Catskills Weekend Itinerary
This post contains affiliate links, including Amazon affiliate links. If you purchase through these links, I may earn a commission at no extra cost to you. As an Amazon Associate, I earn from qualifying purchases. Thank you for your support!
Looking to spend a weekend in Roxbury, NY?
Tucked into the Western Catskills, this artsy little hamlet packs a ton of charm into a few walkable blocks. Think historic churches, a gorgeous village park, indie cafes, and one of the most wonderfully over-the-top places I’ve ever stayed.
And you’re never far from the outdoors. Within a short drive you’ll find some of the best hikes in the Catskills, a restored fire tower with 360-degree views, a waterfall you can literally walk to from your room, and a family-owned ski mountain.
This is exactly why I created the below guide. By the end, you’ll have an epic Roxbury itinerary mapped out — no planning required.
🏨 Quick tip: Top Catskills accommodations like The Roxbury Motel book up quickly during busy seasons, like summer and peak leaf-peeping. Make sure to book in advance for the best rate and most room choices!
How To Get To Roxbury NY
Roxbury is less than a three-hour drive from New York City, making it an easy weekend escape.
Most travelers take the NYS Thruway to Exit 19 (Kingston) and then follow scenic Route 28 west through the Catskills to Margaretville, where you’ll pick up Route 30 north to Roxbury.
You’ll want a car for this trip. Roxbury’s Main Street is walkable, but the best hikes, restaurants, and neighboring villages are a 10- to 40-minute drive away.
If you need to rent a car, I recommend using Discover Cars to quickly compare your rental options.
When To Visit Roxbury
Roxbury is a year-round destination, though each season has its own appeal:
- Fall (my favorite!): Peak foliage typically hits in early to mid-October, turning hikes like Giant Ledge into a sea of color. This is also when the Roxbury Motel goes all-out with Halloween decor.
- Summer: Swim in the Stratton Falls pool, paddle nearby lakes, and browse the Saturday Pakatakan Farmers Market.
- Winter: Ski or snowboard at family-owned Plattekill Mountain, then warm up in the sauna back at the motel.
- Spring: Waterfalls are at their fullest — just note that late March through April is mud season, so pack waterproof boots.
Where To Stay In Roxbury: The Roxbury Motel
For a unique Catskills stay bursting with personality, the Roxbury Motel is the perfect pick.
The property has two locations just down the road from each other:
- Roxbury Village: The original property, right in the hamlet, with rooms themed after classic TV and film.
- The Roxbury at Stratton Falls: The newer property, set around an 1848 Italianate mansion, with more fantastical themed cottages and extra amenities — a seasonal pool, a year-round hot tub, and onsite trails to the beautiful Stratton Falls.
The best part? Staying at either one gets you access to both grounds!
I loved staying in Maria’s Curtains at the Roxbury Village location. Themed after The Sound of Music, highlights include a giant soaking tub, an incredibly comfortable bed, and sumptuous robes and slippers (you can even keep the slippers!).
Plus, breakfast is included, there are loads of lovely outdoor sitting areas with views, and there’s a Shimmer Spa with a sauna and steam room.
Tip: Visiting in fall? The motel really leans into Halloween with over-the-top decor — plus you get gorgeous foliage views right from the properties.
➡️ Click here to check rates and availability at the Roxbury Motel!
The Perfect Weekend In Roxbury Itinerary
Now that we’ve gone over some of the many fun things to do in Roxbury, let’s lay out a suggested itinerary. Follow the below for the perfect Roxbury weekend getaway or tweak it to fit your interests!
Friday
Afternoon: Explore the village. If you arrive early, stretch your legs in Roxbury’s historic hamlet. Its Main Street was listed on the National Register of Historic Places in 1988, and a hamlet-wide designation followed in 2003, thanks to its abundant 19th-century architecture. A few stops worth making:
- Jay Gould Memorial Church: This early English Gothic church, built of St. Lawrence marble and dedicated in 1894, is named for Roxbury-born railroad tycoon Jay Gould.
- Kirkside Park: Walk around back to this 14-acre park, once the estate of Gould’s daughter Helen Gould Shepard, and cross its rustic footbridges over the East Branch of the Delaware River.
- Roxbury General: Wrap up your stroll at this Main Street shop, where you can browse locally made gifts, pottery, and jewelry.
Check in at the Roxbury Motel. Check-in runs from 4pm to 8pm. Coming later? Just let them know and they’ll send after-hours check-in instructions (it was easy!).
Dinner. A few restaurants are within walking distance of the Roxbury Motel.
- Chappie’s is a casual spot for burgers, wings, pizza, and salads.
- The Old Mill serves dinner inside a historic mill building and is known for its crab cakes, goat cheese beet salad, and house Roxbury Mule.
Tip: Restaurants around Roxbury keep limited hours and popular spots book up on weekends, so reserve ahead when you can. If you’re arriving late, plan to pick up food along the way. Depending on which route you take to Roxbury, you can grab a pizza at MaMa’s Trattoria in Hunter or Oakley’s Wood-Fired Pizza & Grill in Arkville.
If you don’t mind driving 15 minutes, my top pick is Oda Wine Garden in nearby Margaretville — a Balkan eatery with an outdoor patio and stellar wine list. I love the trofie pasta in mushroom ragu sauce!
Evening: Grab a nightcap. Swing by Union Grove Distillery in Arkville, about 15 minutes from Roxbury, for craft cocktails and house-brewed Calico Outlaw beer under the same roof. I recommend trying the Catskill Mountain Maple Spirit made from locally produced Tree Juice Maple Syrup. The distillery is open until 9pm on Fridays, when they also serve pizza!
Saturday
After a delicious continental breakfast at the Roxbury Motel, get ready for a day of hiking.
Morning: Giant Ledge
Giant Ledge is my favorite hike in the Catskills — especially in fall, when you’ll get a colorful panoramic view over the trees.
The trailhead is on Route 47 near Big Indian, about 37 minutes from Roxbury. Choose your distance: about 3.2 miles round trip to the first ledge, 4 miles round trip to see all of the ledges, or 7.1 miles round trip if you continue to the Panther Mountain summit. Plan on 2 to 3 hours for the ledges.
You’ll gain about 1,000 feet of elevation, and it’s steep and rocky in sections, but overall it’s a moderate hike with a huge payoff.
Tip: It can get crowded, especially during fall foliage season, so arrive early to snag parking. Luckily, there are multiple ledges to enjoy the views — even during peak season, I got one all to myself!
If you’re comfortable hiking solo, this is a good trail as it’s well marked and popular.
Lunch: The continental breakfast bag from the Roxbury Motel is hearty — I actually saved mine and ate it for lunch on the trail! Prefer a sandwich? Grab one at the Margaretville Deli & Market, which is right on the way to the trailhead.
Afternoon: Balsam Lake Mountain Fire Tower
I recommend tacking on another hike to take in even more Catskills beauty! There are so many great Upstate NY hikes to choose from, though one recommendation is Balsam Lake Mountain via the Dry Brook Ridge Trail.
This moderate 6-mile out-and-back trail takes you along a scenic forest path that follows an old fire road. It’s pretty gradual until the final push, which brings you to a 47-foot fire tower with gorgeous 360-degree views over the tree line and peaks. It’s one of only five remaining fire towers in the Catskills!
There’s a picnic table at the base of the tower where you can enjoy your lunch.
Alternative activities (no big hike required):
- Take a scenic drive: Roxbury sits right on Catskill Scenic Route 30, a 61-mile drive that follows the East Branch of the Delaware River. Head south through Margaretville to the 16-mile-long Pepacton Reservoir, where the Route 30 bridge offers big water-and-mountain views, then detour to the cute village of Andes before heading back.
- Shop the market: Browse the Pakatakan Farmers Market at the historic Round Barn on Route 30 in Halcottsville. Local farmers sell produce, meat, fish, cheese, bread, and plants, while artisans offer jewelry, quilts, and woodwork. It runs Saturdays from mid-May through late November.
- Get views without the climb: Stroll a flat section of the Catskill Scenic Trail, or visit Boyhood Rock, where Roxbury-born literary naturalist John Burroughs’ gravesite looks out over rolling Catskills hills.
Dinner: The Print House in Fleischmanns
Located in the quaint village of Fleischmanns, you can do a little shopping at vintage boutiques like Formerly (vintage clothing, furniture, art, and design) and Two Doors Down (a curated vintage and lifestyle shop) before getting dinner.
The Print House has great craft cocktails alongside beer and wine. The Harvest Salad is hands down the best salad I’ve ever had! I also really enjoyed my shrimp scampi.
One thing: this spot books up, so make a reservation if possible. I went at 5pm on a Saturday without a reservation and couldn’t get a table — though luckily there was space at the bar!
Tip: If you need drinks or snacks for the room, nearby Sam’s Country Store has lots of options.
Evening: Spa time
The perfect way to end a day of hiking is to ease those sore muscles. The Shimmer Spa at Roxbury Village has a sauna and steam room, and the Crooked Cabana at the Stratton Falls location adds a hot tub. Depending on the season, the properties also have fire pits.
Sunday
Morning: Stratton Falls
After breakfast, enjoy the easy trails around The Roxbury at Stratton Falls, which are only open to guests of either Roxbury property. While you can see the falls in 20 minutes, give yourself an hour to also check out the cottage designs and explore the different viewpoints around the waterfall. It’s really beautiful!
If it’s summer, you can also swim in the property’s in-ground pool.
Late morning: Coffee & a history fix
Grab a latte and something to go at Watershed, Roxbury’s go-to cafe for great coffee and breakfast eats like bagel sandwiches, overnight oats, and grain bowls — plus they sell clothing and gifts like Roxbury sweatshirts, unique cards, and cute journals.
Afterward, pop by Kirkside Park if you missed it Friday.
History buff? Head a few minutes outside the village to learn about John Burroughs (1837–1921), the Roxbury-born naturalist and essayist who was one of the most famous nature writers of his day. More specifically, you can visit:
- Woodchuck Lodge: Burroughs spent his last 10 summers (1910–1921) at this rustic farmhouse, built by his brother in the 1860s, writing and hosting famous friends like Thomas Edison and Henry Ford. It’s now a National Historic Landmark with onsite nature trails. Time your visit for Wild Saturdays, a free monthly program series (May through October) with expert talks, guided walks in the nearby woods, and lessons on Catskills history and wildlife.
- Boyhood Rock: Just down the road from the lodge is the John Burroughs Memorial State Historic Site, a state-managed park home to Boyhood Rock, the giant boulder where Burroughs spent hours as a kid gazing over the hills. He’s buried right beside it. A short trail leads from the park entrance to the memorial area, which still has a beautiful view of the Catskills.
Before heading home: Browse Rick’s Barn for antiques or stock up on local goodies at Roxbury General for the drive back.
Other Things To Do In Roxbury
Have more time, or visiting in a different season? Add these to your trip:
- Roxbury Arts Group: This hub of local culture hosts gallery exhibits, performances, workshops, and artist talks. Check the calendar before you go.
- Kirkside Park events: Time your visit for Turn of the Century Days, a vintage base ball match, or summer fireworks in this restored park.
- Plattekill Mountain: Visiting the Catskills in winter? This family-run ski area features about 40 trails and an 1,100-foot vertical drop.
- Pakatakan holiday market: In November, the market’s Round Barn location also hosts a holiday market.
- Catskill Scenic Trail: A flat, 26-mile rail trail on a former railroad corridor, open for walking, biking, horseback riding, and cross-country skiing.
What would you add to this Roxbury NY itinerary?
