Attractions & Things to Do in Hudson Valley Wine Country
Hilltop House Bed & Breakfast is nestled atop a gentle hill with several neighboring dairy farms in New York’s Dutchess County, just 3 miles from the Connecticut border. Its country town locale in Amenia, NY is hub to some of the best boarding schools on the east coast and the culture they radiate. Clever shops dot all the towns in the area; antiquing is rampant, with shops of all sizes (don’t be afraid to negotiate), and the inevitable yard sale for the curious!
Add to that, attractions such as Sharon Playhouse’s summer stock featuring musical productions, wing shooting and horse trials in Millbrook, Lime Rock racetrack’s SCCA racing, fly fishing on the Housatonic River, hiking the New York to Connecticut crossover of the Appalachian Trail, biking on the Harlem Valley rail trail, fine dining and beer and wine making, as well as distilleries within a 15 to 30-minute drive. You’ll discover that our bed and breakfast is the perfect destination for your trip to the Hudson Valley.
Dining
Amenia
- Isabela- (Seasonal Bistro; ½ mile)
- Panacea- (Homemade pasta; 1 mile)
- Lantern Inn – (Pizza; 3 miles)
- Thai Baan - (5 miles)
Dover Plains
- Old Drover’s Inn - (Colonial Tavern; 13 miles)
Wineries, Breweries & Distilleries
Sample some of the Hudson Valley’s best wines at local Dutchess County Wine Trail and Connecticut Wine Trail vineyards!
Art, History & Theatre
- Four Brothers Drive-in Movie Theatre
- The Wassaic Project
- The Moviehouse Millerton
- Sharon Playhouse (Has a summer musical theatre schedule)
- Dia:Beacon Art Museum
- FDR Home & Library
- Vanderbilt Mansion
- Staatsburgh State Historic Site
- Olana
Shopping
Pack a picnic for a memorable cultural outing across the Massachusetts border at famed Tanglewood, summer home to the Boston Symphony. Shop till you drop at the outlet stores at Lee Premium Outlets.
Antiques
- Millerton Antiques Center is a bustling two floors of antiques and curios with some great buys! Open 10-5 every day except Wednesday.
- Millbrook Antiques Mall is open Monday through Saturday 11am to 5pm & Sunday 12pm to 5pm.
- Amenia boasts a few of its own great shops too.
Outdoor Activities
Fly Fishing
The mighty Housatonic River is a great place to fly fish. Both fly fishing and wing shooting are offered at Orvis Sandanona.
Tamarack Preserve - Upland Shooting, Angling and Sporting Clays.
Horses and Farms
- Elk Ravine Farm - Interactive farm tour
- Lilymoore Farm - Alpaca treks and farm tours
- Spend the afternoon at a horse show watching Olympic-level talent.
- Millbrook Horse Trials
- Silo Ridge Masters and Highlands Cup
Lime Rock Park
Lime Rock Park is the country’s oldest motorsport road racing venue, in operation since 1956. It’s located in Lakeville, CT, just 15 mins. from Hilltop House Bed & Breakfast. Uniquely surrounded by a natural park of gently sloping hills, it’s very family oriented; you can enjoy your own picnic while watching the race. (Bring your own chairs and blankets, baskets, etc., since at Limerock, there are no stands!)
Lime Rock Park is the country’s oldest motorsport road racing venue, in operation since 1956. It’s located in Lakeville, CT, just 15 mins. from Hilltop House Bed & Breakfast. Uniquely surrounded by a natural park of gently sloping hills, it’s very family oriented; you can enjoy your own picnic while watching the race. (Bring your own chairs and blankets, baskets, etc., since at Limerock, there are no stands!)
Nearby Towns
Nearby the B&B, you’ll find towns and villages in the Hudson River Valley and Litchfield County, CT that are yours to explore during your stay. Each place has its own unique character. Here are a few that deserve a visit.
Millerton, NY is 8 miles north and has become a popular destination and weekend spot in the Hudson Valley. It’s loaded with trendy shops and restaurants and is a perfect destination for a bike ride on the Harlem Valley Rail Trail.
Ten miles to the west is Millbrook, NY with its charming tree-lined Main Street filled with boutiques and cafes.
A little further to the northwest is Rhinebeck, NY (about 35 minutes). It’s a bigger town with lots of shopping and great restaurants and an old-time general store that will bring back memories to us older folks.
Then 12 miles southeast to Kent, CT, you’ll find another charming Main Street and all the boutiques and eateries that you’d be delighted to find in a small New England town.
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