A small hamlet within the town of Delaware, Callicoon lies at the edge of Sullivan County, where the Delaware River divides New York and Pennsylvania. Once a hub that connected the town to more populated spots along the river, Callicoon is now a popular destination for visitors and those seeking a rural, scenic place to live.
Callicoon was first settled by Dutch hunters in the 1600s, who named the area “Kollikoonkill,” meaning wild turkey creek. The river has continuously been a focal point of the community: In the 1760s, the hamlet was a source of fresh-cut timber. Logs were bound together before being sent down the river to sawmills. In the 1840s, the Erie Railroad laid tracks alongside the waterway to connect the Great Lakes with the East Coast. While Callicoon dates back several centuries, there are few buildings older than 1888, when fire engulfed most of Main Street, forcing residents to rebuild.
Family Life
Children attend schools in the Sullivan West Central School District. In the 2023-24 school year, the district had a total K–12 enrollment of 1,022 students between an elementary school in Jeffersonville and a middle/high school in Lake Huntington.
Annually, Visit Callicoon (the area’s business association) puts on an array of free events that welcome all ages. On June 8, catch the 30th Callicoon Tractor Parade on Lower Main Street; after, you’ll find a barbecue at the Delaware Youth Center (DYC). July 20 is the 5K River Run, a fundraiser for the DYC. Visit on July 26 for the Country Fair, a full day of live music, art, food, shopping, carnival and lawn games, pony rides, and much more.
The DYC offers year-round activities for kids and adults, including swim classes, pickleball, line dancing, and holiday events. The 2025 children’s summer program starts on June 30 and runs Monday through Friday from 9 a.m. to noon for seven weeks.
On the Town
Although small and rural, Callicoon has several shops to peruse on a weekend visit. On Lower Main Street alone, you’ll find Lee Hartwell Antiques selling accessories and homewares; Callicoon VINTAGE, a secondhand store filled with clothing, art, and records; Black Walnut Mercantile, an artisan home shop and cocktail bar by The Farmhouse Project; Litt Home & Book; Spruce Home Goods; Wool Worth yarn shop; The Callicoon Pantry refillery; and Peck’s Market grocery store.
After shopping, grab a bite at Callicoon Brewing Co., Callicoon Caffè, Callicoon Wine Merchant & Tapas Bar, the tasting room at Catskill Provisions Distillery, northern German restaurant Navor Koken, or Peppino’s Restaurant, Bar, and Pizza. Just north of the hamlet on Wagner Lane lies Seminary Hill Orchard & Cidery, which offers its craft cider alongside farm-to-table food at the tasting room and restaurant.
Get Out There
Given its position on the Delaware River, it’s no surprise that Callicoon and the surrounding area offer several opportunities to enjoy the water. Lander’s River Trips’ northernmost launch point is on Dorrer Drive, providing canoeing, kayaking, rafting, and tubing outings, as well as riverside camping at Skinners Falls in Narrowsburg.
Every Sunday, head to the Callicoon Farmers’ Market held on Creamery Road; a “producer-only” market, all the vendors—from farmers to bakers, artisans, and more—operate within 75 miles of the hamlet. In town, there’s also the circa 1948 Callicoon Theater, a hub for new movies, old favorites, local film festivals, and live music.
While it has begun to foster a more robust dining and shopping scene in recent years, Callicoon remains a community that revels in nature. Look around—the views of the Delaware River Valley and the Catskills speak for themselves.
Neighborhood Stats
(Callicoon Hamlet)
Area: 0.4 sq. mi.
Population: 206
Average home listing price: $675,700
To find a real estate agent in Callicoon or any Hudson Valley town check out near-me.hvmag.com/realtors.
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