The Catskills are bigger than they seem, so when people refer to the famed area, they often mean wildly different places, miles apart. The famous Borscht Belt, for example, is but one of three “neighborhoods”—located in the southern Catskills, its environs stretching from the Overlook Mountain Wild Forest down through lower Ulster County and into Sullivan County. (Think: dilapidated old resorts and lake communities.) Meanwhile, in the northern Catskills, in Greene County, Hunter Mountain reaches up into to Windham Mountain, Elm Ridge Wild Forest, and down into Schoharie County. (Think: swimming holes and skiing.) Finally, there are the western Catskills, extending from northwestern Greene County to Delaware County, nearly to the Pennsylvania state border. (Think: farms and the Delaware River.) Conquering those combined 5,892 square miles in one weekend is next door to impossible. But sampling all three “neighborhoods” in three days is feasible and fun—although a car is imperative, despite the proliferation of Trailways bus stops in various Catskills towns. Any road trip to the Catskills is well worth it, particularly in the fall, when the colors become dreamy shades of red, orange, and gold.
Arrive at the Village of Roxbury in Delaware County, in the western Catskills, and check into the quirky, stylish Roxbury Motel (2258 County Route 41), with its on-site spa. Rooms vary from approximately $90 for a single in the off-season to $695 for the Archeologist’s Digs, an Indiana Jones-errific suite that accommodates six guests.
Grab hearty sandwiches to go from Cassie’s Café (53535 NY-30, Roxbury), the local go-to for diner offerings, then head to Kirkside Park (Kirkside Drive, Roxbury) and follow the 14-acre public park’s meandering brook through historic properties, over Adirondack log bridges, to historic properties, including the Jay Gould Reformed Church (53837 NY-30, Roxbury).
Have some time to spend back in town? Peruse the wares at Roxbury General (53538 Foute 30). Buy something with “Roxbury” printed on it to spruce up the décor back home and mystify visitors. Then lace up those hiking boots, and hit the Catskill Scenic Trail (Hard Scrabble Road & NY-30, Roxbury). The trail follows the tracks of the Ulster and Delaware Railroad, and its flat grade makes it perfect for cycling, too.
OPTIONAL DETOUR FOR VIEW SEEKERS
Want to get even more rural right away? Head toward Bovina, about 40 minutes west of Roxbury, leaving time to make a couple of stops along the way toward dinner there. First stop: Woodchuck Lodge (Burroughs Memorial Highway, Roxbury). Noted naturalist John Burroughs’s house tours take place on Saturdays and Sundays, but the historic site remains open weekdays. Next stop: Plattekill Mountain (469 Plattekill Road, Roxbury). Take a chairlift ride, because there’s no better way to take in the autumn views of the Catskill Mountains than from a sky-high vantage point.
In Bovina, the Brushland Eating House (1927 County Route 6) serves a seasonal, rustic meal that focuses on simple, hearty, and communal dining. Be sure to make reservations, because, despite its geographic obscurity, this place also offers a few boutique hotel rooms and is often packed. Back in Roxbury, enjoy a nightcap at Public Restaurant and Lounge (2318 County Route 41). The bar serves up festive cocktails and bar treats until 11pm Friday and Saturday.
Head over to West Kill in Greene County, about 45 minutes from Roxbury, for spending Saturday night. The ultimate destination for the night is Spruceton Inn (2080 Spruceton Road), a casual, comfy mountain establishment offering kitchenette rooms (a sensible option since there are no eateries nearby). But don’t miss out on the good stuff by racing from destination to destination. Take scenic Route 28 south, with stops in Margaretville for breakfast at the popular Crazy River Café (42287 Route 28), featuring goodies baked in-house; book shopping at Bibliobarn (40 Church Street); Pine Hill (home of Belleayre Mountain) for gawking at the cool old architecture; and Shandaken at Blue Barn Antiques (Roses Brook Road) for checking out the antiques.
Keep going south to Phoenicia, pausing for repast at the Phoenicia Diner (5681 NY-28, Phoenicia), a hip eatery with a high-quality diner menu (be on the lookout for Kelsey Grammer). Stop at the Mystery Spot (72 Main Street), a record and vintage clothing store that bills itself as an “antique emporium & odditorium,” where both locals and celebrities shop.
OPTIONAL DETOUR FOR VARIETY-SEEKERS
Continue south to the Ashokan Reservoir for views, and then stop at Fabulous Furniture (3930 NY-28, Boiceville) to check out local artist Steve Heller’s atomic-age creations and hand-made furniture. If you’ve still got some drive left in you, continue into Woodstock, meander along Tinker Street by car or on foot, and then head back toward West Kill to check in at Spruceton Inn.
Spend the rest of the afternoon exploring Hunter and Tannersville (stopping at the local grocery for tomorrow’s breakfast items), grab a grass-fed Angus burger from Mama’s Boy Burgers (6067 Main Street, Tannersville), take in the magical fall foliage around Colgate Lake, and wander around Mountaintop Arboretum, open year-round, dawn to dusk, free of charge. If you have time, hike the short trail to the former site of the Catskill Mountain House at North South Lake, visit Kaaterskill Falls, or pick your own pumpkins and apples at Story Farms (4640 NY-32, Catskill).
Unwind at Spruceton Inn with a craft beer, wine, or cider at Conan’s Corner, the on-site bar. For dinner, make a reservation at Peekamoose Restaurant (8373 NY-28, Big Indian), 20 minutes away. Often touted as the best restaurant in the Catskills, Peekamoose, owned by Devin and Marybeth Mills, offers farm-to-table fare from an ever-changing menu.
Cook breakfast in the room before bidding farewell to Spruceton Inn. Proceed east to Saugerties via Platte Clove Road, which is closed from November to April, leaving time to take to the trails and spy some waterfalls at Platte Clove Preserve in Elka Park. Hang out in Saugerties for brunch at Love Bites (69 Partition Street). Enjoy the tiny restaurant’s eclectic (and extensive) selection of seasonal breakfast/brunch/lunch fare while sitting front and center to Saugerties’ main drag, the perfect spot to plan your next great Catskills adventure.
OPTIONAL DETOUR FOR GHOST HUNTERS
Head into the southern Ulster County Catskills to Napanoch, home of the Shanley Hotel (56 Main Street), the area’s only (as far as we know) haunted B&B offering paranormal investigations. That’s right: ghost-hunting. Book an overnight stay in the reportedly haunted 19th-century inn and participate in an actual spirit hunt. Even if you don’t spend the night, you can still join the hunt at a reduced rate, but what fun is that? Don’t forget: BYOEMFM*.
*Bring Your Own Electro-Magnetic Field Meter