Between New York City And Albany Is A Serene Hamlet With Small-Town Charm And Appalachian Trail Accessibility

In the stretch of the Hudson Valley between New York City and Albany, there's a wealth of small towns that have the unique appeal of being both within easy driving distance to major cities while retaining a more rural, slow-paced charm. They range from New Paltz, New York's hippie town with a European-style shopping street, to the popular getaway of Hudson, a trendy small city called the "Downtown of Upstate." Venture a bit further east of the Hudson River, and you'll find even more hidden gems among the rolling hills of the valley's eastern farmlands. One of those is the hamlet of Dover Plains, a pretty village within the larger township of Dover. With a small footprint, you could reasonably walk across the hamlet's main drag in around 30 minutes. In that half an hour, you can see a legendary cave, a well-preserved Federal-style house, and grab a bite to eat at one of its lovely restaurants.

Dover Plains was once part of a sparsely populated area known as "the Oblong," formally becoming a town in 1807. But the hamlet really developed around the mid-1800s, when, in 1848, the Harlem Railroad was extended to reach Dover Plains, which for a few years was the final stop on the route. The railroad allowed local industries for iron, marble, and dairy to flourish, followed by an influx of immigrants plus the establishment of the hamlet's first bank. Today, you can still take the Metro-North Railroad's Harlem line from Grand Central Station to Dover Plains in about a two-hour journey — by car, it's about an hour and 40 minutes from Grand Central. If you're flying in from out of state, the nearest major airport is Stewart International Airport, located about an hour southwest of Dover Plains by car.

Dover Plains captures the scenic, pastoral side of New York's historic Dutchess County, known for its serene hills and art trails. One of its most famed sites is the Dover Stone Church Preserve, which has 4 miles of trails that round off at a truly awe-inspiring sight: a tremendous rock formation in the shape of a cathedral's arch, with the Stone Church Brook flowing gently from its maw. You'll find this wonder on the west side of the village, with parking available off Route 22. You wouldn't have a small-town wonder without its small-town legend, and this one goes that in the 1600s, a Pequot leader named Sassacus hid inside the Stone Church's cavern to avoid being captured by the British Army. Visitors today can climb inside the cavern, where you'll be greeted by a stunning 30-foot waterfall flowing down into the stone fissure.

Nature lovers will also be pleased to find that Dover Plains is part of the designated Harlem Valley Appalachian Trail Community, with trail connectors from the village. Though the trail itself is a bit further south from Dover Plains, starting from the village is a good option when the Metro-North Railroad doesn't go to its designated Appalachian Trail stop (it only stops there on weekends). There are turnouts along Route 22 that connect to the trail, including to the iconic Dover Oak, the largest oak tree on the trail, about a 15-minute drive from the hamlet center.

Whether you're making a pit stop along the Appalachian Trail or day-tripping from New York City, Dover Plains has some great places to stay and eat. Old Drover's Inn is a charming find, housed in what was once a tavern built in 1750. The beautiful, Colonial-style building was the secretive love nest of Elizabeth Taylor and Richard Burton in the 1960s. Today, it's a well-rated bed and breakfast with a rustic, lantern-lit restaurant called The Tap Room.

There are other options for dining, too. Ana's Family Restaurant has 4.5 stars on Google and rave reviews, with many praising its prices and friendly staff. The restaurant specializes in Latin American cuisine with a diner-like setting. When your sweet tooth is craving a fix, check out Kelly's Creamery, the town's artisan ice cream hotspot that comes with a mini golf course. The ice cream comes in over 30 flavors, plus there are some inventive seasonal flavors, like autumn's apple pie and pumpkin pie specials. Around Halloween, the mini golf course is also outfitted as haunted mini golf.

If you're willing to explore a bit outside of the village center, every visitor to Dover Plains should make time to stop at Soukup Farms, a modestly sized maple syrup facility with beautiful grounds. The farm upholds a local legacy of maple-tapping, something the Iroquois people have been doing around upstate New York since before settlers arrived. It has over 3,000 taps and is open for visitors during Maple Weekends in March (typically the last two weekends of the month), as well as the farm's special two-day Harvest Festival in the fall.