Midweek Two Night Getaway at Hilltop House B&B

Bikers enjoying the rail trail

Two Night Midweek Getaway (Tuesday and Wednesday Nights, or Wednesday and Thursday Nights) in one of our charming and cozy rooms.

The Experience:
Hilltop House Bed & Breakfast is nestled atop a gentle hill in Dutchess County just 3 miles from the Connecticut border. Its country town locale is hub to some of the best boarding schools and the culture they radiate. Add to that attractions such as TriArts summer stock, wing shooting and horse trials in Millbrook, Lime Rock NASCAR and SCCA racing, fly fishing on the Housatonic, the Appalachian Trail, biking on the rail trail, an abundance of fine dining and the arts abounding in the area, and you will discover that our B&B is the perfect destination for your trip to the Hudson Valley.

Amenities include:
Complimentary WIFI in all rooms, gourmet cooking from the chef/innkeepers, Double, Queen Sized or King Side Beds available. Private or shared baths. Use of the B&B’s Bicycles.

Package Includes:
A Four course breakfast on the porch, or by the fire (weather dependent)
A $100 voucher for Monte’s Restaurant
Overnight stay at the B&B
Use of the B&B’s Bicycles
Includes 2 Metro North round trip tickets from Grand Central Station to Wassaic and back
Price: $559 two nights (double occupancy) plus applicable taxes

Suggested Itinerary:
Enjoy a delicious breakfast at the Inn

Ride to local Millerton (the B&B will provide Bicycles). Millerton offers a selection of shopping, antiques and galleries to browse, and was voted one of the coolest small towns in the country by Frommer’s.

Window Shop and eat lunch at one of the many local eateries. Harney & Sons is a favorite local lunch spot, as well as offering a world class selection of fine teas and specialty gifts, or visit Irving Farm Coffee Roasters and enjoy a lovely cup of coffee and lunch before heading back to the Inn.

If exploring the local Rail Trails is more enticing than window shopping for the remainder of the afternoon, guests can check out the Harlem Valley Rail Trail which offers 15 paved miles of trail meandering through stunning rural Dutchess and Columbia County landscapes.

Head back to the Inn and freshen up for dinner and then walk to Monte’s, a 10 minute easy walk from the inn, and enjoy fantastic farm to table dining cooked by Monte’s Executive Chef Dafna Mizrahi, 2015 Chopped Champion.
After dinner take a stroll or a short drive, over to the Four Brothers Drive In for a movie or come back and relax on the wraparound porch.

On Day 2 check out Dover Stone Church on your way back to the city. (Additional train fare required) or further explore the Harlem Rail Trail.

To book this B&B overnight package, call the B&B directly at 845-789-1354 at least ten (10) business days in advance and mention the Midweek B&B Getaway package.

Train in Foliage Season


Come to the Hilltop House B&B, a Hiker’s Paradise

Deer in the woods

Hilltop House Bed and Breakfast is the perfect basecamp for a weekend or mid-week getaway if you like to explore the outdoors. Situated close to the border of CT, it gives access to both the best of the Hudson Valley hikes as well as the trails in the beautiful Litchfield County portion of Connecticut. Book your room at our award winning Bed and Breakfast, then head outside to find your favorite trails. You could spend days exploring the trails and never get tired of the views, ranging from those along the Hudson River to those in the wooded hills of the surrounding areas, the area is home to some of the best hiking opportunities in the Northeast.  The scenic beauty of this area will keep you coming back time and time again.

A great way to document a hike or walk, spring, summer, fall or winter is create a documentary or do a photo scavenger hunt of your trip. This is fun thing to do with kids or without! Bring your camera and a trail map, and create a list of things to look for and document them as you find them by making notes on your trail map, and then corresponding them to your photos. This is fun to share with friends and family on Facebook, or create a blog post with your photos and notes.

Some suggested things to look for on a hike.

  • Animal tracks in the mud, sand or snow
  • A historical marker
  • Trail Signs
  • Wild Flowers
  • Interesting dead trees or branches
  • Pine cones
  • Berries
  • Vines
  • Moss
  • Seeds or seed pods
  • Ferns
  • Hole in a tree
  • Unusual shaped leaf
  • Caterpillar
  • Squirrel
  • Bird
  • Butterfly or moth
  • Feathers
  • Insects
  • Spider webs
  • Birds nests
  • Insects on a tree
  • Animal holes in the ground
  • Animal Scat
  • Deer and/or Deer Tracks
  • Frog or Toads
  • Leaf with insect holes

Don’t forget to bring sunscreen, bug spray and plenty of water for hydration. Back up cell phone chargers are also recommended. Happy Hiking! We look forward to hearing about your adventures!

There are hundreds of hikes locally, here are a few of our best links to help you plan the perfect hiking tours when you come to stay!

Hudson Valley Views

Hike the Hudson Valley

The Best Hiking Trails and Paths in the Hudson Valley, New York

Hudson Valley Hiking

Hiking in Litchfield County

Litchfield County CT Hiking Trails & Land Trusts

Litchfield, Connecticut Trails and Maps

Local Events of Interest:
August 23-28, 2016 – Dutchess County Fair
For six days each August, the bucolic fairgrounds on Route 9 in Rhinebeck plays host to nearly half a million patrons. The second largest county fair in New York State is the showplace for agriculture in Dutchess County. Over 144 +/- acres of finely manicured gardens and grass create the beautiful setting for thousands of farm animals, agricultural exhibits and horticultural displays.

September 1-5, 2016 – Lime Rock Park Labor Day Weekend Events
Since 1983, Lime Rock Park has held its annual celebration of historic motoring significance by combining authentic-car vintage racing with a prestigious Concours d’Elegance. It’s an event unique to North America in that the racing and the concours are all on one property during one major vintage and historic event. The historic racing on Lime Rock’s classic 1.5-mile, 7-turn circuit on Friday, Saturday and Labor Day Monday sandwiches the Sunday in the Park Concours d’Elegance, held on the track’s 2,200-foot Sam Posey Straight. In the past decade the Historic Festival has added a 17-mile race car parade-and-rally over local roads and through three town centers, ending in a community street fair in nearby Falls Village, as well as creating a 1,000-car Gathering of the Marques car show that’s held concomitant with the concours.

Hike along the falls