Callicoon, Catskill Mountains
Courtesy of the Sullivan County Government

Everyone who has lived in New York City during the deep summer months knows this: Heat trapped between skyscrapers mixed with over eight million residents can make summertime more suffocating than enjoyable. Luckily, less than a two-hour drive away lies a number of quaint towns nestled in the Catskill Mountains where those looking for an escape can take refuge. Here are the six most noteworthy Catskill towns to check out on your next summer venture out of the city.

1. Roscoe

Roscoe, NY Catskill Mountains
Photo by Darren McGee, Courtesy of New York State Department of Economic Development

Roscoe, New York is tucked within the Catskill Mountains right off NY Route 17. It is also known as Trout Town USA after being named the “Ultimate Fishing Town” of the U.S. by the World Fishing Network in 2011, but there is definitely more to Roscoe than its trout. Its downtown area has a colorful walking district and is full of small Victorian-era buildings, many still bearing their original signs, giving the town an incredibly rustic feel. Set amidst the rolling Catskill Mountains, the town has a vibe that makes visitors feel as though they are being taken back in time.

This feeling can also be found at the self-declared “World Famous” Roscoe Diner, where a variety of American college flags are on display, and they serve old-fashioned “taste of America” diner classics including eggs, bacon, burgers, and ice cream sundaes. Nearby are the Roscoe Beer Company and the Prohibition Distillery. Visitors can head to the distillery to try some local liquor or grab a seat at the brewery to enjoy the cozy atmosphere. 

Located just outside of the town are two of Roscoe’s biggest attractions. One of which is the mysterious Dundas Castle, also known as Craig-E-Claire Castle. The castle is nestled in the woods, tucked off the main road and nearly hidden from passing cars. It was built in the early twentieth century, though according to the small amount of known information on the castle, it was never actually lived in as the owner died shortly before it was completed. The site is on private property and is unable to be visited, although that has not stopped many curious explorers in the past century from climbing the steep forest hills to get a glimpse of the decaying castle forgotten in the trees. 

Just down the road from Dundas Castle is the “town” of Agloe, New York. Although, it’s not actually a town at all. Made famous by John Green’s book Paper Towns, Agloe was a fictional town used by mapmakers to fool plagiarizers. In reality, all there is to see of Agloe is a sign just off NY Route 206 indicating the Agloe General Store that does not actually exist. Nonetheless, it makes Roscoe a unique travel destination.

2. Livingston Manor

Livingston Manor, Catskill Mountains
Photo by Darren McGee, Courtesy of New York State Department of Economic Development

Livingston Manor, located just southeast of Roscoe, is slightly bigger than its neighbor. Considered the birthplace of flyfishing, there are many creeks and streams where one can enjoy the peace and quiet of casting a line and feeling the breeze on their face. The most famous creek is Willowemoc, supposedly where the sport began. There is even a museum dedicated to the history of the sport, the Catskill Fly Fishing Center. The Center is located on a 53-acre campus that features a Welcome Center, the museum, the Wulff Gallery which displays the works of Lee and Joan Wulff, the Heritage Craft Center which features a fully operational bamboo rod-making shop, a covered pavilion, casting fields, a pond, a trail system, and river access.

Like Roscoe, “The Manor” (as it’s known locally) is a walker’s paradise with many spots springing up that are worthy of a trek. The Kaatskeller is a hip local restaurant with lots of outdoor garden seating, live music, and a funky upstairs lounge.

The nearby Upward Brewing Company is another place where you can sit back and relax away from the confines of the city. This scenic brewery is tucked amongst the mountains and visitors can enjoy a beer, grab a bar bite, sit outside on their large sunny lawn overlooking a lake, or even go for a quick hike up Beer Mountain. The long list of relaxing activities makes this an ideal place to visit with family or a group of friends. 

The town also has a variety of BBQ eateries to check out including (but not limited to) Van Smokey Meat Shop and The Smoke Joint where travelers can check out some Catskill grilling. Two spots to stay for those looking for that cozy yet chic vibe include The Arnold House and The DeBruce. Both are owned by the same family, and guests staying at either of these places will experience peaceful mountain luxury both on a culinary and comfort level.

3. Callicoon

Callicoon, Catskill Mountains
Courtesy of the Sullivan County Government

Callicoon, located on the New York-Pennsylvania border, has more hipster influence than the previously mentioned towns. Its Main Street is lined with antique and consignment shops, albeit pricier ones than can be found in Roscoe or Livingston Manor. There is a farmer’s market located behind Main Street at Callicoon Creek that one can visit every Sunday from 11 a.m. until 2 p.m. Here visitors can try local wines, jams, and cheeses while taking in some Catskill charm.

Located on the Delaware River, Callicoon also has many water sports to offer including kayaking, canoeing, tubing, and anything else one could find themselves wanting to do on a large river. Its downtown area is decked out with shops and historic buildings all still proudly showing off their vintage exteriors. The most impressive one may perhaps be the Western Hotel located on Main Street. An old Victorian mansion, it was originally opened as an inn in 1852 and has ten guest rooms that are still used today by guests from all over who come to find a quaint yet charming getaway destination.

4. Narrowsburg

Narrowsburg, Catskill Mountains
Courtesy of the Sullivan County Government

Narrowsburg, just a twenty-minute drive down the Delaware River from Callicoon, is a small community with many ways to kick back and enjoy a hot summer day. The smallest town in the group, Narrowsburg has a recorded population of only 372 residents according to the United States Census Bureau’s 2020 census. This allows Narrowsburg to retain a quiet vibe to counter the city’s very unquiet summer buzz. Much like Callicoon, Narrowsburg has water activities on the Delaware River and a variety of restaurants located on its banks. One of the more popular places to eat on the river is The Laundrette, complete with outdoor seating overlooking the water and a menu that includes tacos, a variety of wines, a long list of pizzas, and even organic hot dogs. 

5. Jeffersonville

Jeffersonville, Catskill Mountains
Courtesy of the Sullivan County Government

Jeffersonville is known for its picturesque rural-town beauty with streams, lakes, open grasslands, and other natural charms. One of the Catskill town’s most well-known features is its Stone Arch bridge. Built in the late 19th century, this bridge still stands covered in grass amidst a park fittingly named the Stone Arch Bridge Historical Park. The park has a playground for children, a peaceful swimming area in the creek beneath the bridge, and even a hiking trail.

Jeffersonville also has many new small businesses opening up and a number of restaurants which add to its appeal. Visitors looking for a more active trip can step out of their comfort zones and learn to horseback ride at Bridle Hill Farms for an interesting weekend away activity.

6. Bethel

Photo by Darren McGee, Courtesy of New York State Department of Economic Development

Bethel is the home of the 1969 Woodstock Music Festival, so if anyone is looking for a “weekend of peace and music” this is the place to be. Where once the iconic festival took place, now the open fields are part of the Bethel Woods Center for the Arts, where many other music festivals are still held. The original festival has a memorial located on the plot of land where it once took place that is open to be visited by the public. Also located in Bethel is the Bethel Woods Museum which commemorates Woodstock and gives visitors an idea of what it would have been like to attend the iconic festival. 

Outside the site of Woodstock, the town of Bethel retains its artsy legacy with many colorful bars and hippie-themed shops including the Woodstock Oasis convenience store, where you may even have a chance to get a hamburger with a peace sign pressed into the bun. With its exciting history and colorful influence, Bethel clocks in as the largest town on the list regarding population with a whopping 4,255 residents according to the 2010 census.

Next, check out these must-visit places in the Catskills and find out how you can ride an abandoned railroad track in the Catskill Mountains on a bike!