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Small Town Weekend Getaways in Upstate New York

Small Town Weekend Getaways in Upstate New York

Fall is almost here, and it’s one of the best times of the year to explore all that Upstate New York has to offer. The leaves change into beautiful colors wherever you look, and there’s a world of outdoor fun you can explore with your family and friends. While you may want to visit the bigger, more popular cities in the area, there are several small towns hiding in plain sight that hold just as much fun. Stop into one of these towns on your next weekend road trip and see what’s in store.

Six Upstate New York Getaways


If you’re traveling along the eastern shore of the Hudson River, you’ll find Beacon waiting for you during your drive. Beacon is Upstate New York’s haven for the arts and exploration, and you’ll find creativity wherever you look. It’s best known for being the home of Dia Beacon, a contemporary art museum that hosts a bookshop and cafe inside. Other artsy spots include the “Doctor Who”-themed restaurant The Pandorica, the Beacon Flea Market and Story Screen Beacon Theater Drive-In. If you want to find adventure outside of the arts, head down to the river to explore the ruins of Bannerman Castle and other vintage mansions along the water.

Bannerman's Castle Beacon New York |
Bannerman’s Castle&nbsp;(Courtesy <a href=””>Hunter S.</a>)


While most people might be familiar with the Catskill Mountains, they might not realize that there’s an actual village called Catskill hidden inside them. The town is best known for being the setting of Washington Irving’s famous short story “Rip Van Winkle,” and there’s plenty of fun to have throughout the area. If you want to see the town from above without heading into the mountains, step onto the Hudson River Skywalk and get a scenic view from above. A different kind of trail you can walk on is the Catskills Beverage Trail, as the town is home to a number of breweries and cideries where you can taste some of Upstate New York’s finest brews.

Catskill New York |
Catskill (©Andrew S.)


Saugerties, located just a few miles from the famous town of Woodstock, has played a significant role in the music and arts scene of the Hudson Valley. The nearby town’s historical significance as a hub for 1960’s counterculture and music helped put Saugerties on the map as well, drawing in artists and musicians looking for a creative community. In recent years, Saugerties has also gained attention for its annual Woodstock 50 music festival, held at the picturesque Winston Farm just outside of town. The town has a number of sites inside that help it stand out, including the massive sculpture park Opus 40 and Saugerties Lighthouse, a combination of a lighthouse and bed & breakfast visitors can explore during their upstate visit.

Saugerties Lighthouse New York |
Saugerties Lighthouse (©Reid Buchanan)


Another small town in the Catskill Mountains you can visit is Hunter, but you’ll find it in a different spot than Catskill. Hunter is higher up in the mountains and makes sure to take your trip to new heights. It’s best known for New York Zipline Adventure Tours, where you can strap onto a zipline and fly through the Catskills like never before. If you’re looking to slide down the mountain, hitch on some skis in the wintertime and take a trip to Hunter Mountain Resort. Complete your getaway with a visit to one of Hunter’s bed & breakfasts and restaurants, and you’ll have one mountain vacation you’ll never forget.

North–South Lake, Hunter New York |
North–South Lake, Hunter (©Clay Banks)


If you’re taking a trip near Rochester, head to the Finger Lakes region and stop in the beautiful town of Canandaigua. This is the perfect waterfront getaway, as it hosts a number of aquatic activities, from visiting Kershaw Park along the lake to splashing at Roseland Waterpark. If you’d like to stay dry during your trip, you can also walk through the gardens at Sonnenberg Gardens & Mansion State Historic Park or sip on local wine along the Canandaigua Lake Wine Trail. Be sure to stop by during one of the number of festivals throughout the year to give yourself the perfect small-town experience.

Canandaigua Lake New York |
Canandaigua Lake (©J Dean)