Drive over to Bear Mountain State Park next. (We recommend stopping in Tuxedo or Sloatsburg for a quick bite first.) Inside the park near the Bear Mountain Inn, you’ll find the trailhead at Major Welch Trail and Hessian Lake. Take the red-circle-on-white Major Welch trail up varying terrain to an AT intersection. Turn left, then head up to the summit, where the very first AT blaze was set in 1923. Continue on the AT down, pausing to admire the volunteer-laid stone steps that offer an easy descent. If you’re up for more hiking, continue on the AT across the Bear Mountain Bridge, and go to the trailhead just north of the bridge; this will take you up a mountain called Anthony’s Nose. From here you’ll have a wonderful view of the bridge and Bear Mountain. If you’ve had enough hiking after Bear Mountain, it’s a short but windy drive along “The Goat Trail” (aka Route 6) to Peekskill and many food and drink options; you can also head back to Warwick.
Bear Mountain trail markers. Flickr/ALH1
Food & Drink
Dottie Audrey’s Bakery/Kitchen in Tuxedo Park is one of our favorite cafes in the Hudson Valley for a scratch-made breakfast or lunch; you can’t miss with any of their salads, sandwiches, or baked goods. For dinner in Peekskill, try Taco Dive Bar or Peekskill Brewery at the riverfront, and Whiskey River in the downtown area. Not too far north from the trail in Warwick is the ever-popular Warwick Valley Winery & Distillery, a great post-hike spot where you can share a bottle and listen to live music on weekends from 2–5 p.m.
If you want to finish your day trip in luxury, check into the Bear Mountain Inn, the 1915 Adirondack-style structure with 15 queen rooms and king suites and a spa. Their 1915 Restaurant is currently closed, but it’s worth a visit another time. In Peekskill, get pampered at The Abbey Inn & Spa, one of the Valley’s newest — and hottest — boutique hotels.
Fahnestock State Park. Photo by Skip Pearlman
– Trip 3 –
Fahnestock State Park and Pawling
For a rustic day trip in the remoteness of Putnam and southern Dutchess counties, start with a hike in Fahnestock State Park (Route 301 and Taconic State Parkway). About 10 miles of the AT are inside the park; the best way to hike it is via an easy up-and-back (trailhead at Route 301 and Canopus Creek, Hopewell Junction) that meanders by the creek. Go south from the trailhead 2.2 miles to an intersection with Sunken Mine Road, then turn around and follow north back to the trailhead.
After hiking in Fahnestock, travel east on Route 301 toward Pawling or head up the Taconic to East Fishkill. Grab a sandwich or two wherever you go, then beeline to the only train station on the AT, the Metro-North Appalachian Trail stop (991 Route 55, Pawling). From here, it’s a decent 2.3-mile uphill hike west (south on the AT) to the Dover Oak, the more than 300-year-old tree, the largest oak on the AT.
After photographing the old tree, continue another 0.8 miles south on the AT to Cat Rocks, a great spot to sit and check out a picturesque view of the Taconic Mountains. Just be careful out there: it’s a steep hike. When you’ve soaked it up, head back to the train station and finish the night with a hearty meal in Pawling.
Food & Drink
Need a post-hike refuel? Drive to the rustic Patsy’s Roadhouse in Hopewell Junction for big ol’ burgers, plus sandwiches and salads. For a quick but loaded sandwich, thru-hikers and visitors alike head over to Tony’s Deli in Pawling. A traditional sit-down meal can be had at McKinney & Doyle Fine Foods Café, also in Pawling. Offerings include duck breast, rack of lamb, and local trout. At Daryl’s House, you can get food, drinks, and live music (for a limited audience, at present). And who knows: owner Daryl Hall himself may stop by. For a no-frills nightcap, visit O’Connor’s Public House, a happy local haunt with dark-wood bar and homey environs.
Just a 12-minute drive west of Fahnestock is the easy-in, easy-out Countryside Motel. This affordable motor lodge has clean rooms and is accessible for day hikers. Go west on 301 and you’ll hit the village of Cold Spring, and more upscale options like Hudson House River Inn (a great place for a riverside brunch) and The Pig Hill Inn Bed and Breakfast. The quaint Station Inn in Pawling has thoughtfully country charm, plus a common area and coffee/tea services.
Kent Falls. Photo by Timothy Malcolm
– Trip 4 –
Kent and Salisbury
You’ll want to spend time in the quintessentially small town of Kent, CT, if only to walk Main Street and visit a café. Before that, take on Caleb’s Peak and St. John’s Ledges (trailhead at River Road near N. Kent No. 1 Road, Kent), atop the ridge hugging the Housatonic River. Follow the Appalachian Trail south, and uphill, to the St. John’s Ledges overlook, then continue to Caleb’s Peak. Scrambling is likely, but the view of the Housatonic Valley is worth it.
After adventuring in Kent, drive north up Route 7. You can stop at Kent Falls State Park to picnic and approach Kent Falls, the tallest waterfall in the state, with 250-foot falls spanning over a quarter mile.
For a late-afternoon hike, continue on Route 7 North, to routes 112 and 41, to Salisbury’s Mount Riga State Park. Here, the test is Connecticut’s own Bear Mountain (trailhead at Route 41 near Foothills Road, Salisbury). This 6.7-mile hike has a tough climb of more than 1,400 feet starting at the blue-blazed Undermountain Trail. That’ll bring you to the Paradise Lane Trail, which you’ll continue on until reaching the Appalachian Trail. Head left on the AT to reach the summit via a doable scramble; the top is a little piney with a giant rock pyramid perfect for gazing at the view. Continue on the AT until reaching the Undermountain Trail, then turn left, and when you see Paradise Lane again, turn right to stay on the Undermountain. This hike will leave you feeling exhilarated, so a big dinner in Salisbury is in order.
Food & Drink
In Kent, get coffee and bagels — plus loaded and bready sandwiches — at J.P. Gifford Market & Catering Company. Kingsley Tavern is a great bet with its very American cuisine of chops and fish inside a cozy house. And Bull’s Bridge Inn, named after the iconic covered bridge just two minutes down the road, is all creaky wood with a fireplace and a beautiful bar top — a perfect place for dinner and drinks. For dining up north, The White Hart, a New England-style restaurant and inn in Salisbury, has hearty classics like duck confit and half chicken, or you can sit at the restaurant’s downstairs taproom for a cozy experience with elevated pub grub like a lamb burger and black bean chili with cornbread. In the village of Lakeville in Salisbury, chill out at Black Rabbit Bar & Grille, home to friendly bartenders and good craft beer.
No hotel matches the quaint charm of Kent quite like the Starbuck Inn. Stay in a queen or king room; eat a full complimentary breakfast; and enjoy afternoon tea with pastries and tea sandwiches. In Salisbury, you can stay at The White Hart after dining there. Most of the stately rooms, some with four-poster beds, run for closer to $230. Note: In this area of Connecticut, many hotels demand two-night bookings for weekends.
Monument Mountain. Photo courtesy of Massachusetts Office of Tourism
– Trip 5 –
Mount Washington State Forest and Great Barrington
You can spend multiple days exploring the distinctive New England charm and daring heights of the Western Massachusetts Berkshires, but if you were to distill it to a day, start at Mount Washington State Forest. Take the 1.5-mile up-and-back trail to Bash Bish Falls (trailhead at Route 344 after Taconic State Park entrance, Copake Falls, NY), an iconic duo of cascades created by one heck of a boulder, then test your mettle with the Alander Mountain Trail (trailhead at 165A East St., Mount Washington, MA). Follow the blue-blazed trail up a 3.5-mile climb that includes a strenuous final stretch. Go back the way you came. It’s not the AT, but it’s a worthy hike – just listen for rattlesnakes in the dry heat.
Next, head to Sheffield to taste some beer, via Big Elm Brewing, and whiskey, via Berkshire Mountain Distillers. Then head north up Route 7 into Great Barrington, a pretty town with shopping, theaters, and restaurants all calling your name.
After hitting the Main Street stores (find clothing, toys, gifts, and more) and grabbing lunch in town, head another four miles north to Monument Mountain (trailhead at Route 7 near Monument Valley Road, Great Barrington, MA, $5 parking fee). Go up the 0.8-mile Hickey Trail for a serious ascent, then catch the Squaw Peak Trail’s red blazes, which will take you up a scramble to the summit. The top is allegedly where Herman Melville came up with the idea for Moby Dick. After absorbing the views of Western Massachusetts, reverse your steps, but instead of the Hickey Trail, take the 1.5-mile Indian Monument Trail to the lot.
Photo courtesy of The Prairie Whale
Food & Drink
For breakfast or a quick grab-and-go bite, the Marketplace Kitchen and Café in Sheffield hits the spot; breakfast burritos early, paninis later. One eatery you can’t miss is Bistro Box in Great Barrington, though you might drive by it, as it’s on the side of Route 7. Get there early to avoid lines, grab a burger, and enjoy eating it outside at a picnic table. Also in Great Barrington: The Prairie Whale, with its rustic chic and fun cocktails, is like Brooklyn showed up in the Berkshires; and Barrington Brewery & Restaurant, in a very charming country house with old wood everything, is old-school for craft beer, and makes super traditional fare with warm service.
Offering solitude in farmhouse chic environs, Race Brook Lodge in Sheffield has 32 unique rooms, plus an onsite tavern. In the heart of Great Barrington, The Barrington offers several distinct and posh suites like The Appalachian Highway, complete with gold mirrors, a canopy bed, and a glass-top coffee table.