Dover offers mountain views and outdoor recreation near Pawling
Right on New York’s border with Connecticut, Dover is a quiet community in the Taconic Mountains. “It’s just so beautiful. If you like rolling hills and mountains and a quaint little village and a train station, it’s a lot,” says Teddie Leonaggeo, a real estate salesperson at McGrath Realty who has sold homes here for 23 years. “There’s nothing city-ish about it.” Although it’s mostly home to rolling hills, forests and a smattering of local restaurants, Dover and its surrounding communities offer plenty of entertainment for those who enjoy country life and outdoor recreation. “If you want to go up a little north, you can go skiing; if you want go a little south, you can go skiing,” says Judy Albert, a real estate salesperson at Berkshire Hathaway with over 16 years of experience. “You can come to the Town of Pawling. It has a very central location and is a gateway to a lot of other activities.” Dover’s Metro North access also makes it attractive to residents who occasionally travel to New York City.
Popular hiking trails, West Mountain State Forest and athletic spaces
With several small nature preserves and access to the Appalachian Trail, hiking is popular in Dover. One particularly popular hiking trail leads to the Dover Stone Church Cave, a local landmark known for its natural beauty. The hike to and from the cave usually ends up being about 3 miles. At the edge of Dover, West Mountain State Forest is 830 acres, providing plenty of space for residents to hike, bike, ride horses or fish. During winter, there’s also cross-country skiing and snowshoeing, and seasonal hunting is allowed with the right permits. Thomas J. Boyce Park is a more developed green space that offers a large playground with swings, athletic fields for baseball and soccer and courts for pickleball, basketball and tennis.
A quiet atmosphere with the potential for acreage or a suburban vibe
Dover has several clusters of homes with slightly smaller lots and an almost suburban feel, but the rest of the neighborhood has a rural atmosphere. Streets lack sidewalks even in more suburban areas. Hi-ranches are incredibly common here, but there are also many ranch-style homes and New Traditionals. In more suburban areas, homes can still have a little over an acre of land and typically cost between $240,000 and $500,000. More rural houses often have multiple acres and can cost between $370,000 to $1.2 million. Occasionally, restored historic homes with double-digit acreage hit the market for over $2 million.
Dover schools have small class sizes and upcoming updates
The Dover Union Free School District has a B-minus on Niche. The small district consists of just four schools and has a student-to-teacher ratio of 11-to-1. Children can attend Dover Elementary School, which has a C-plus, or Wingdale Elementary School, which has a B. They then move to Dover Middle School and Dover High School, which both have B-minus ratings. In 2020, the district completed renovations on the old high school building, which became the new space for the middle school. They also finished and opened the new building for the high school. The high school’s $18 million athletic complex rehaul is slated to finish up by fall 2026.
Routes 22 and 55, country roads and two Metro North stations
State Route 22 and state Route 55 connect Dover to surrounding communities, with the latter leading east into Connecticut. Dover has two Metro North stations, Dover Plains and Harlem Valley – Wingdale. From these stations, the train reaches Manhattan’s Penn Station in about two hours and 20 minutes.
Local restaurants along Route 22, more options in nearby towns
Restaurants dot Route 22, with pizza places like Cousin’s Café Wood Fired Pizza and Four Brother’s Pizza Inn dominating the culinary landscape. Other options include Anna’s Family Restaurant, which is known for its breakfast and enchiladas, and La Guadalupana Mini Market, which offers tacos and tamales alongside a small selection of groceries. For more dining and entertainment options, residents drive to surrounding towns, which Leonaggeo says are a little artsy. Amenia and Millbrook are both about 12 miles away, so they’re popular choices. “There’s a drive-in movie theater in Amenia, which is the next town up,” she says. When residents need groceries, Amenia has Freshtown Marketplace and Millbrook has Marona’s Market.
Fall apple and pumpkin picking, annual events in nearby towns
Dover is quiet year-round, but there’s plenty to do close to home, from events thrown by nearby farms and the seasonal Millbrook Farmers Market to Amenia’s free summer concert series. “They have a ski area that’s down here in Patterson,” Leonaggeo says. “Especially in the fall, they have a lot of apple picking and pumpkin picking.”
Creeks occasionally overflow during severe storms
Heavy rain can cause the creeks that crisscross Dover to overflow, leading to potential flooding in the area.
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Written By
Christina Norwood
