St. John’s Cliffs, a perfect area to experience Fall Foliage in the valley

Man climbing CliffSt. John’s Cliffs (Less than 30 minutes from the B&B)
Map from the Inn to the Cliffs

St. John’s Cliffs (also known as St. John’s Ledges) are rock formations near the border of Kent and Cornwall, CT. The Appalachian Trail goes along the base of the cliffs and then up around them with some of the most challenging trails in the state. If you are traveling northbound on RT. 9 and look to your left you can see the ledges right across the Housatonic River.

The cliffs were named after Timothy St. Johns, who originally owned the property in the 1800’s, the land is now owned by the National Park Service. If you are coming for the climbing, it’s mostly top-rope and traditional climbing, and consists of two separate climbing areas. The elevation is 950 ft.

If coming for a day hike, you can climb to the top which takes you past the cliffs themselves. It is a steep climb, but has always been well maintained. A word of warning, there are some steep drop-offs, so if you do not do well with heights, it may be wise to skip the trail up. If you are up to the challenge, a gorgeous scenic view of the valley awaits, and you can climb further up to Caleb’s Peak for an even better view of the surrounding area.

The ledges are a hot spot for local climbers because it’s known for having some of the best long slab climbing in Connecticut, so if hiking or climbing isn’t your cup of tea, pack a lunch and come and watch local climbers challenge the faces. For the hikers that would like a little more scenery and less of a step challenge, there is a dirt road that follows the Housatonic River for several miles with some lovely views of the river, and several small trail offshoots to check out.

The ledges are a beautiful place to check out in the fall as the views from up top are incredible during foliage season. Be sure to bring a camera (or your smart phone) to catch some terrific pictures.

Check out this Youtube video taken at the Ledges:

If hiking the Appalachian Trail from Kent (a 3.5 – 4.5 hour hike), visit for a trail map.

If you are a climber, visit and for some climbing tips/points on the ledges.

And check out some great photos of the area and views from the top at

Man climbing cliffDirections to the cliffs:
From Kent center, head west on Route 341 and over the bridge. Immediately after the bridge make a right onto Skiff Mountain Road. After approximately a mile bear right onto River Road. Which is a dirt road. Go 1.6 miles until you reach the parking area on the left. Follow the white-blazed Appalachian Trail from parking area. To reach the lower climbing area look for a trail, on the left, 35 feet past the trail mapbox. To reach the upper climbing area, stay on the Appalachian Trail until it passes directly by the bottom of the cliff.

Local events:
Saturday, October 15 and Sunday, October 16, 2016
The Sheep & Wool Festival
The Dutchess County Sheep and Wool Growers Association, 501(c)3 promotes year round events that focus on farming fiber and food. Their premier event is the New York State Sheep and Wool Festival.

Sunday, October 30, 2016
Family Fun @ the Kent Pumpkin Run Dotted Line
Kent Connecticut, the #1 town in New England for fall foliage is hosting the 40th annual Pumpkin Run on October 30. Entertaining for participants and spectators alike, the fun begins at 11:15 with a kids “Fun Run” that is followed by a 5 mile run at noon. In the Halloween spirit, many prizes are awarded for costumes as well as for finishing times. The gorgeous course has its own reward at the end as all are invited to the Post-race Party with great food, face painting for the kids and gift certificates from Kent’s charming shops.


Cathedral of the Pines, New England’s Largest Old-Growth Pine Forest

Giant White PinesThe Cathedral of the Pines or Cathedral Pines as it is also known, is a little known hiking spot located less than 30 minutes from the Bed and Breakfast. The Pine stand covers over 42 acres, and while devastated by three tornadoes in July of 1989, the remaining trail still covers the intact portion of the stand, and is well worth the visit.

Cathedral Pines was New England’s largest stand of old-growth white pine, hemlock trees and northern hardwoods, and while the tornadoes did substantial damage, many of the trees survive and you can still experience the size and beauty while walking under the canopy of trees. One of the reasons to take this hike is to see the after effects of Mother Nature at work, and to see the stand itself slowing recovering from the devastation. White pines are unusual to see in this part of Connecticut, and most of them are 200 years old with some being at least 300 hundred years.

The Cathedral Pines forest itself was established between 1770 and 1800. It was part of a thousand-acre farm inherited by Major Seth Pierce (1785-1881), Following Pierce’s death in 1881, Frederick Kellogg sold the Pines to John Calhoun, who vowed to preserve the majestic forest. The Pines at different time periods were also called Calhoun’s Pines and the Calhoun Grove.

In 1967, the children of John Calhoun deeded the 42-acre Cathedral Pines to the Nature Conservancy, which established the forest as a research area protected from human influence in its development. Rather than harvest high quality lumber from felled trees, the Nature Conservancy allows them to decay naturally. Cathedral Pines was declared a National Natural Landmark in 1982. The Nature Conservancy while studying the Pine Stand observed that the pines were being slowly replaced by hemlock trees. The slow transformation of the forest from pine to hemlock was sped up dramatically in 1989 by the devastating tornadoes.

While visiting the Pine Stand listen for woodpeckers and owls at dusk, bring bug spray and good hiking shoes. While the trail is an easy one, there are quite a few downed branches and dried pine needles that make walking in sandals quite uncomfortable.

Essex Hill Road, Cornwall, CT
Google Map Link


A Bit of History and Art to Explore this Fall

Mason ToolsA trip to the area is never complete without a visit to the Eric Sloane Museum & Kent Iron Furnace. The Museum is on the National Register of Historic Places and a Connecticut State Archaeological Preserve. The Museum is owned and operated by the State of Connecticut Department of Economic and Community Development, State Historic and Preservation Office.

Eric Sloane (1905-1985) was an artist, author and illustrator of over 30 books, and a collector of American artifacts. In the museum itself, Sloane’s studio has been recreated with his painting easel and jars filled with paintbrushes, alongside examples of his works in the adjacent art gallery. Sloane built a cabin in the pioneer style modeled after Noah Blake’s “Diary of An Early American Boy”, an 1805 diary published by Sloane. Eric Sloane’s collection of hand tools is displayed in the museum building gifted to the State in 1969 by Stanley Works, a Connecticut-based tool manufacturing company, to mark their 125th anniversary. The collection tells a fascinating story about historic times and the great American heritage of craftsmanship. The Kent Iron Furnace, also on the museum property, began production of pig iron in 1826, and continued production for almost 70 years. A display explaining the local iron industry is in the museum lobby as well.

This past summer, the museum become one of a handful of museums in the country with an heirloom variety apple orchard. The orchard, envisioned through collaboration between the Friends of the Eric Sloane Museum and Peter Montgomery, a Silicon Valley executive turned horticulturalist, was installed on the grounds of the Eric Sloane Museum of Kent this past April.

Eric Sloane Museum & Kent Iron Furnace (20 Minutes from the B&B)
31 Kent Cornwall Rd, Kent, CT
Hours: Fri-Sun: 10:00 am – 4:00 pm through October 31, 2016
$8 adults
$6 seniors (60 years +) & college students
$5 children (6-17)
Free children 5 and under
Discounted admission for schools and groups by appointment.
Free admission to active duty military members and up to 5 family members with ID

Save the Date! October 8th, 2016 for an apple tasting event sponsored by the Friends of the Eric Sloane Museum with culinary teacher and chef Anne Gallagher. This free event will run from 11:00 am to 1:30 pm. Please RSVP by calling the museum at (860) 927-3849 and leaving a message with your name, contact information and number of people who will attend.


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