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, and fine dining and beer and wine making, as well as distilleries within a 15-30-minute drive. You’ll discover that our bed and breakfast is the perfect destination for your trip to the Hudson Valley.





Pine Plains

Hyde Park 

Kent, Lakeville & West Cornwall CT 


Maple Syrup 

Cooking Class

Hey, food lovers! What are you doing on the weekend? If you love to cook or bake or are a budding wine connoisseur, you need to be at the CIA. After just a few hours in a cooking class or wine seminar, you just might discover a culinary passion or talent you didn’t even know you had. For you noshing kind of foodies, The Institute serves lunch and dinner from an outstanding menu of fresh and fine foods. We love eating there whenever we get a chance, and the bakery is fabulous for special take outs! Writing this reminds us of how long it’s been, and that we need to get back there. The CIA is high up on the banks of the Hudson, with a spectacular view, accessible from its walkways.

The Culinary Institute of America
1946 Campus Drive
Hyde Park, NY 12538
Contact Continuing Education:
800-888-7850 / 845-452-2230

Click here for weekend course schedules

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


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.


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 thru 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. In Cornwall Bridge, CT, you’ll find Housatonic River Outfitters. 860-672-1010

Fly fishing trips are offered at Orvis Sandanona.


Spend the afternoon at a horse show watching Olympians jumping.

Riding Stables


Autumn? Hunt for pheasant and quail at Orvis Sandadona (12 miles). Orvis Sandanona has the oldest licensed shooting grounds in the nation. Sporting clays, shooting and fly-fishing schools, private shooting lessons, and a pro shop.


Bike to Millerton—a town with shops to explore, and restaurants to enjoy on the Harlem Valley Rail Trail. Hop onto our bikes and start. Just 200 yds. away.


The Appalachian Trail can be accessed off Route 4, less than 10 miles away in Sharon, CT. Connecticut’s Blue Trail runs in Cornwall a few miles east of the Appalachian Trail, and there’s a great mountainous loop overlooking the Housatonic, to climb, just north on Route 7 opposite Housatonic Meadows Camp Area.


The Housatonic River is the place to be! Clarke Outdoors (16 miles, up Rte 7)

Ski Resorts

Forty minutes to 4 ski areas—Catamount (due North in South Egremont, MA), Butternut (Northeast in Great Barrington, MA), Thunder Ridge (South in Patterson, NY) and Mohawk (due east in Cornwall, CT), where they invented snow making!


Wethersfield Garden

Season: Wethersfield Garden is open from June through September. Hours: Wednesdays, Fridays and Saturdays, noon to 5 PM. Last admission 4:30pm. (845) 373-8037.

Innisfree Garden

Season: Innisfree Garden is open from May 7 to October 20. Hours: Wednesdays, Thursdays and Fridays, 10 AM to 4 PM. Saturdays, Sundays, and legal holidays.

Many local garden clubs conduct tours throughout the summer.

Audubon Society

Sharon Audubon Center and Emily Winthrop Miles Wildlife Sanctuary, connecting people with nature. Immerse yourself in nature; snap some stills at the Audubon Sanctuary in Sharon, CT., only 6 miles away.

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!)

The late Paul Newman, a Connecticut-er himself, is said to have called Lime Rock his favorite place to race. Even you can enroll with the Skip Barber School and get your thrills and skills in gear! Every Labor Day weekend, Lime Rock holds its annual historic festival featuring vintage cars and a parade of sports cars. One can enroll in a snow-driving skills course in the winter. Open year round, a calendar of events is on the park’s website.

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 (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.

Private Schools