Woodstock, New York
Hands down, one of the best small New York towns to visit near NYC. Although the town has been famed for the historic Woodstock Festival (which actually took place in Bethel), Woodstock still offers the friendly hippie vibes, a unique art scene, and that charming 60s culture. When I first entered Woodstock, I stumbled upon a circle of drummers playing music, and seconds later one of them invited us to play with them. Woodstock is also a wonderful place to connect with friendly locals.
Waterfalls & Hikes: Go hiking in one o the many nearby trails or waterfalls such as Kaaterskill Falls or Fawns Leap. Or, if it the weather permits, jump into one of the natural swimming holes nearby for a refreshing swim. Downtown Area: Stop at one of the many delicious restaurants in Woodstock. If you like tacos, I recommend Oriole. Woodstock has a ton of charming restaurants from Asian fusion cuisine to restaurants perched along the water with outdoor picnic tables
Phoenicia, New York
Once you arrive at the atmospheric town of Phoenicia, you may easily forget you're anywhere near NYC. There is a quiet stillness, a green fragrance, and lush vibrance that this town exudes, perfect for a relaxing day trip from NYC or a spa weekend getaway.Esopus Creek River - Phoenicia is located along the Esopus Creek River which offers visitors opportunities for tubing or rafting. Hiking - Go hiking along the many trails of Phoenicia.
Greenport, Long Island
This port town is located towards the far end of Long Island's North Fork; a region renowned for its vineyards/wineries, small farms, restaurants, and flower fields.Tea Garden - Have high tea in this beautiful garden where you can order beautiful herbal infusions and pastries like biscuits or lavender macaroons. Downtown Area - Walk through the area to really absorb the vibe of this port town.
Shelter Island, Long Island
Shelter Island is special. Not just because it's lush, quaint, underrated, and located just minutes from Long Island by ferry-but there is also a unique history of Greek and other European immigrants who moved here in the 1900s and have shaped the island's modern-day ambiance. Today, the island retains a unique multicultural heritage while also being home to some of the most expensive and lavish homes in the country.Mashomack Preserve - 2,000+ acres of nature reserve with marshes, forest & creeks.
New Paltz, New York
New Paltz is special. As soon as you enter the town you'll see a small Dominican restaurant at the foot of the main street two hours north of NYC. That alone wins major points for this small artistic college town in the Catskills. For foodies, art lovers, cultural enthusiasts, and outdoor aficionados, New Paltz is one of the best small towns in New York to visit and makes for one of the best day trips from NYC.Stroll the downtown area - New Paltz is home to several restaurants and shops in their expansive downtown area. Their restaurant selections range from Turkish to Dominican food! And there are several side streets to explore for art or shopping as well. Hiking - New Paltz is at the foot of so many different hikes from NYC to choose from. The most popular ones being in Minnewaska State Park Preserve and Mohonk Preserve.