This Is The Most Hospitable Town In New York
Shandaken, New York's most hospitable town, feels like the kind of Catskills town that welcomes you the moment you arrive, with its friendly hamlets and stunning mountain scenery. Made up of 12 hamlets, the town blends outdoor adventure with local character, from skiing and swimming to art and scenic hiking trails. At the heart of it all is Phoenicia, Shandaken’s largest hamlet and main center, known for its arts scene and access to Slide Mountain, the highest peak in the Catskills. In summer, Pine Hill draws visitors to Belleayre Beach, while neighboring Highmount becomes a hub for winter fun at Belleayre Mountain. Big Indian adds local lore through the legend of Winnisook and Gertrude, plus a long-standing place in Catskills storytelling and settlement-era history. Spend a little time here, and it is easy to see why Shandaken calls itself the land of “Four Seasons of Fun.”
Phoenicia: The Largest Hamlet
Once the hub for the Ulster and Delaware Railroad, Phoenicia remains the hub of activity in the town of Shandaken. Relive the railroad in its heyday through photos, exhibits, and artifacts at the Empire State Railway Museum. Displays trace the history of communications inventions like photography, the telegraph, and the typewriter, all of which helped keep the trains rolling. If you visit from May through October, you can ride the original rails on Rail Explorers pedal cars with electric assist, all along the Esopus Creek. Take in a live performance, musical act, film, or special event at the Phoenicia Playhouse, which has a year-round schedule. The VARGA Gallery & Studio sponsors the Phoenicia Festival of the Arts, Friday, August 21, through Sunday, August 23, 2026, which will also include the Phoenicia Film Festival. Phoenicia is also a shopper's haven. Check out The Blue Barn and Phoenicia Art & Antiques for eclectic finds from multiple merchants.
Slide Mountain, the highest peak in the Catskills at 4,180 feet, can be accessed near Phoenicia on Route 47 via the Slide Mountain Trail. It is of medium difficulty for the intermediate hiker. The summit itself is heavily treed and therefore does not offer a view, but other ledges near the top provide clear views of the peaks and valleys below.
Pine Hill: Saratoga of the Catskills
When the railroad reached Pine Hill in 1872, tourists took the train out to Pine Hill for its fresh air, relaxing lifestyle, and upscale grand hotels, earning the hamlet its nickname, "Saratoga of the Catskills." The big attraction is Belleayre Beach, located at Pine Hill Lake. Enjoy a lakeside picnic and water activities, including swimming, single- and double-kayaking, canoeing, stand-up paddleboarding, pedal boats, and aqua trikes. The beach also has volleyball/badminton courts, horseshoe pits, and hiking/biking trails. In the evenings, Bellayre often has family-friendly movie nights, live music, and events.
Open from late June through Labor Day Weekend, the beach charges a modest fee ($20/vehicle for up to four people and $5 for additional persons duriing 2025 season). Season passes are also available, covering entrance fees and a half-price boat rental. Seniors 70+ receive free admission during the week and a discounted rate on weekends. Fishing is free with beach admission but requires a New York state fishing license, which can be purchased at a local store. Anglers catch trout, bass, perch, sunnies, and other varieties at the lake.
Highmount: Skiing and More
Right next door to Pine Hill hamlet is Highmount, the place for winter sports like downhill and cross-country skiing, snowboarding, and snowshoeing. Belleayre Mountain Ski Center features upper and lower lodges, 50 trails for skiers of all levels, and eight lifts, including a fast, enclosed gondola. Buy your lift ticket online so you essentially have a reservation, as they do sell out. The Ski Center also offers season passes with lots of perks, frequent skier cards, and lesson packages for kids and adults.
Ride to the summit on the Catskill Thunder Gondola in summer and fall from June 27 through October 12. (Check their website for operating times.) Belleayre's Disc Golf course has lower and upper nine-hole courses, which are free to use, but you must bring your own discs or buy them in the gift shop. The 20-foot-tall Belleayre Climbing Wall features three climbing paths for climbers of different levels and an automatic, hydraulic belay system to lower climbers gently. The cost is $10/person and includes two climbs.
Big Indian: A Love Story
This hamlet was named after the Native American Winnisook, a 7-foot-tall member of the Munsee tribe of the Lenapes. Winnisook fell in love with Gertrude, the daughter of an early settler, and she fell in love with Winnisook. The glitch was that she was betrothed to Joseph Bundy -- or, in some accounts, the couple was actually married. However, Bundy was said to be an unsavory character, and Gertrude was miserable in the relationship. So Winnisook and Gertrude eloped and went to live with the Munseees. After the fearless Winnisook led a raid on the local farmers' sheep, a revenge posse that included Bundy set out to find the raiders. During the skirmish, Bundy himself shot and killed Winnisook, who was buried in the area where Big Indian hamlet is today.
Big Indian is more than a love story, however. One of the most iconic Catskills hikes is the trek to Giant Ledge and Panther Mountain. Giant Ledge is actually five ledges, and hiking to all five is about 4 miles out and back. It is considered a moderately strenuous hike on steep, rocky surfaces that are often muddy. Continuing on to Panther Mountain adds about 2 miles round-trip to the hike. The small parking lot fills up fast, so start out early to ensure a space. Families with small children will enjoy Big Indian Park's playground with swings, a jungle gym, a merry-go-round, and a pavilion that can be rented.
Mt. Tremper: Visitor Center
If you are looking for more to do, places to stay, where to rent gear, directions, maps, or anything about the Catskills, stop at the Catskills Visitor Center (CVC) on Rt. 28 in Mt. Tremper hamlet. The building showcases exhibits about the area and is staffed daily from April 1 through November 30, and Friday through Monday from December 1 through March 31. Hours are 9:30 AM to 4 PM year-round.
The grounds are open year-round during daylight hours, even when the CVC is closed. Climb the 80-foot-tall fire tower and hike three trails, each .5 miles long out and back. CVC Esopus Creek Trail leads to the banks of the creek, is ADA accessible, and is one the whole family can enjoy. The CVC Upper Ridge Trail climbs a slope to a picnic area, showcasing trail-building techniques along the way. CVC Interpretive Loop Trail circles the Visitor Center, is ADA accessible, and has panels explaining the history and ecology of the area. All three trails leave from the CVC building. For a break from the trails, visit the Emerson Kaleidoscope, the largest in the world, in Mt. Tremper's Emerson Resort.
Dining and Lodging
Hikers often substitute several snacks for a meal while hiking, or break for a picnic meal along their route. But when you want to eat a whole meal prepared by someone else, Shandaken's hamlets provide numerous options. The Phoenicia Diner has served locals and visitors for decades with staples like meatloaf and classics with creative twists like chorizo mac & cheese. Local inns often offer lodging and a restaurant, like the Shandaken Inn and Clubhouse Restaurant and Bar. Their menu changes daily but often includes a Wagyu burger and sides like truffle French fries.
Campgrounds are located throughout the area, like the well-known Black Bear Campground in Phoenicia and Allaben Campground in Allaben hamlet. Both offer RV, tent, and group sites, and Allaben has primitive camping sites as well. For boutique indoor lodging, rent a Lushna at the Eastwind Oliverea Valley hotel in Big Indian. The Scandinavian-styled, fully glass-fronted cabins are shaped like tents for a cozy view of the surrounding wilderness. For a more pampered experience, Mt. Tremper's Emerson Resort has both rustic suites at The Lodge and more upscale suites at The Inn, along with spa and salon treatments, a fitness center, and fine dining at their Catamount restaurant.
What to See Nearby
If your goal is to at least see all 12 of Shandaken's hamlets, you can drive, bike, or hike through Mt. Pleasant, Woodland Valley, Chichester, Shandaken, Bushnellsville, and Oliverea. Although there is a lot to see and explore in Shandaken's hamlets, the famed town of Woodstock is less than a 30-minute drive from Shandaken; take NY-28 E and Wittenburg Road to NY-212 E. While the famous 1969 Woodstock festival was actually held in the town of Bethel, Woodstock is a vibrant town itself. Take in a live performance at the historic Woodstock Playhouse or live music at the more intimate Bearsville Theater, and explore the shops on Tinker Street.
Summing it All Up
With so much to see and do in Shandaken and its hamlets, you could take weeks to explore it all. Since it does offer Four Seasons of Fun, you might plan to visit each season. In the winter months, plan a ski trip to Belleayre Mountain for its beginner-to-Olympic-level runs. Hike the trails in the spring, being sure to bring gear for ice and mud to prepare for any conditions. From the end of June on, take part in the water sports at Belleayre Beach and ride the gondola for spectacular aerial views. Once fall arrives, it's time for leaf-peeping as the forest turns brilliant hues of yellow, orange, red, and gold. Any time of year is a good time to visit Shandaken, New York's most eclectic, most varied, most hospitable town.
