One Of New York's 'Best Small Town Main Streets' Resides In This Charming Catskill Mountain Hamlet

Near the New York-Pennsylvania border, the charming hamlet of Callicoon sits in the western Catskills, where the Delaware River, winding creeks, and vibrant seasonal foliage create a picturesque setting. But the scenery isn't the area's only reason to visit. Country Living named Callicoon home to one of the best Main Streets in America, recognizing its walkable downtown, historic architecture, and independently owned businesses.

Historic Dutch Colonial-style buildings frame the walkable street lined with locally owned storefronts and independent boutiques. Places like Callicoon VINTAGE sell unique antique furniture, while Ragtime Clothing Exchange thrifts second-hand fashion. Along the same path, you'll find casual farm-to-table cafés like The Kitchen Table Cafe, or fancy sit-down meals at the Black Walnut. The latter also operates as a mercantile, stocked with locally sourced goods, adjacent to its chic lounge and dining room. 

Rather than relying on chain businesses, Callicoon's downtown has preserved the mom-and-pop spirit and character. It's the kind of place where locals know the owners on a first-name basis, which makes the strip feel more like home than a bustling tourist center. The surrounding scenery in the Catskills is just an added bonus as to why it's one of the most favorable hamlets in the U.S.

Callicoon's Main Street sits near the confluence of the Delaware River and Callicoon Creek, where waterfront views add to its enchantment. Along the Delaware River, visitors can spend the day kayaking, canoeing, tubing, fishing, and even eagle watching. Scenic back roads wind by the creek, leading to the Stone Arch Bridge – a picturesque landmark set within a 20-acre park. 

Locals say the best time to visit for outdoor fun is autumn. The oranges and reds blanket the hillsides, and the hiking trails make it all possible to view. Although Callicoon is small enough to explore in an afternoon, it's worth spending a full weekend to experience both its historic downtown and the surrounding Catskills. For an overnight stay, nearby Callicoon Hills, a scenic cabin resort with swimming spots, makes a convenient base for touring the region within a 15-minute drive.

Public transportation is limited, and only shopping buses run five days a week. It's recommended to rent a car. The closest major airport is Wilkes-Barre Scranton International Airport (AVP), an hour-and-a-half drive southwest, making a rental the convenient option over a rideshare. Also, it's easy to discover more of the Catskills, venturing farther into the Upper Delaware River, a quiet escape that winds through forested bluffs, vintage towns, and trout-filled pools. For more hidden gem hamlets nearby, check out our feature on one of the best small mountain towns with rustic lodges.