Just under 100 miles from NYC, the northeastern edge of Dutchess County is home to open pasture, rolling hills, lush forest, little rivers and picturesque towns. Thanks to the efforts of conversationists, this part of New York remains largely unspoiled — and has been a paradise for lovers of the outdoors for hundreds of years. In fact, this little region in Dutchess County has long inspired radical free-thinking since its founding: from slavery abolitionists who met there in the 1700s, to the transcendentalists who gathered at Troutbeck (where our guide begins) in the 1800s, to the Amenia Conferences in the 1900s which strengthened the formation of the NAACP.

These days, northeastern Dutchess County and Amenia continue to inspire its visitors and residents. When visiting, get the lay of the land on a hike to a mountaintop fire tower, take in the scenery from the longest pedestrian bridge in the world, explore towns that appear to be stuck in time — or simply roam the grounds of the historic Troutbeck hotel. Check out our guide below, then book a trip to find your own inspiration in this beautiful region, 100 miles from New York City.

Where to Stay: Troutbeck in Amenia, NY

The Dunham Suite at Troutbeck. All images by Erin Lindsey/Escape Brooklyn, except where noted.

The historic estate-turned-boutique-hotel Troutbeck is our homebase for this guide. And with rooms beginning around $200 (and topping out at $700), there’s something for everyone. Depending on which building you book, rooms range in price but also layout; the rooms in the original building are more compact but really unique in character, while its modern outbuildings are spacier but more uniform. (By the way, all of them are lovely.) Whatever your preference, pack your fancy-but-outdoorsy garb and pretend you’re being whisked off to your super-rich, super-stylish great-aunts Upstate estate for the weekend — we loved the highbrow vibe here, and you will too.

Guests are likely to get disoriented in sprawling indoors of the main building at Troutbeck; cozy nooks, narrow hallways and sitting rooms with fireplaces abound. In the evening, grab a drink at the hotel bar, then make your way to the dining room for dinner inside Troutbeck’s beautiful restaurant. Outside, the 250-acre estate has tons of outdoor space to roam, too — and with amenities like a swimming pool, riverside bonfires and gazebo, an enormous stone wall-enclosed garden, and a (forthcoming) spa — the designers behind Troutbeck have created the ultimate oasis.

Beautiful grounds and interior design aside, Troutbeck is also rich in history. Dating to 1765, the Tudor-style mansion has been attracting artists, conservationists, and politicos for centuries, hosting the likes of Mark Twain, Henry David Thoreau, Ralph Waldo Emerson and the naturalist, John Burroughs. In the 1900s, Troutbeck hosted the pivotal Amenia Conferences, sparking some important moments in the history of the NAACP and the Civil Rights Movements. To this day, it continues to attract interesting people; guests are likely to leave with some new friends!

What to Do in Amenia, NY: Antique Shopping, Hiking, and Exploring Dutchess County

Fall foliage at the Stissing Fire Tower.

To spend the day outdoors, a hike up to the Stissing Fire Tower is steep but incredibly rewarding. At the top of the trail, climb the firetower for unparalleled 360º views of the Hudson Valley and Catskills. Depending on which trail you take (there are two clearly marked options), you can plan to spend about two hours up and back. Before the hike, take the 10 minute drive to fuel up on breakfast or lunch at The Farmer’s Wife. The very cute cafe in equally cute village of Ancramdale serves breakfast and lunch, but also offers prepared-food takeout. Grab a bite to eat inside, or get something to-go for a picnic on the hike. (Note: open seasonally.)

For a less challenging endeavor, check out the Walkway Over the Hudson in nearby Poughkeepsie. At 212 feet tall and 1.28 miles long, it is the longest, elevated pedestrian bridge in the world. Enjoy by foot or by bicycle, and take in the views of the Hudson River and the nearby Catskill Mountains. Admission to the bridge is free; parking is $5 in the closest lots. From May to October, a stroll around Innisfree Garden is yet another way to take in the outdoors. Recognized as one of the worlds best gardens, the 40-acre property encircles a lake, with several miles of trails that zig zag through a composition of rock, water, wood and sky; highlights include a mist waterfall, an oxbow stream, and a stone arches and stairways. Weather and season permitting, plan on spending a couple hours here; admission is $6-8.

True to its name, the Bottle Shop has entire rooms of antique bottles and glassware. Prepare to dig!

An any-season itinerary includes shopping around the nearby towns of Millerton and Millbrook. Our favorite hidden gem is Bottle Shop Antiques, who stocks a little bit of everything. Be prepared to dig around, as the rooms are literally filled to the brim with antique treasures and architectural salvage. (Great resource for all you DIY-ers!) Next, head ten minutes down the road to Millbrook, with some cool antique shops including Millbrook Antiques Center and Painted Peach; also pop into Alicia Adams Alpaca, where everything is made from luxurious and colorful alpaca wool. After shopping around in Millbrook, head to Millerton, following scenic Route 44 all the way and begin your journey at Irving Farm. The Millerton location of this boutique coffee chain is just a mile down the road from where its roasted — so you know you’re getting the best cup of coffee around. Iriving Farm is located toward the top of Main Street, so park there and make your way down the strip. Don’t miss Terni’s, an authentic old-school general store stocked with everything from hunting magazines to Woolrich blankets and Pendleton shirts — then continue walking down Main Street to Millerton Antiques CenterHunter Bee, Meta 44, Cottage + Camp, Harney & Sons, and more.

True to its roots, the tradition of philosophical exploration in the region is carried on by its many artists, specifically those at the Wassaic Project. The non-profit art center offers arts education, festivals, exhibitions and events, and an artists-in-residency program that attracts crazy-good talent. Check out their event calendar to see what’s going on.

Where to Eat & Drink: Farm-to-Table Restaurants & Local Diners

Canoe Hill in Millbrook, NY. Photo c/o Canoe Hill.

If you’re staying at Troutbeck, don’t miss the opportunity to dine in its restaurant. In mornings, the windows let in tons of natural light and show off the beautiful surrounding landscapes; in the evenings, the warmly lit dining room is just perfect, with a fireplace adding to the atmosphere. No matter the time of day, the space is beautiful, with delicious food to match. Even if you don’t dine here, stop in for a cocktail at the pink-and-copper clad bar, or cozy up in front of one of the many fireplaces.

Between all the little surrounding towns in Dutchess County, there’s a lot of great options for meals while on-the-go. For a classic Upstate greasy-spoon breakfast, look no further than the Millbrook Diner, whose interior is straight out of the 1950’s, with a mini-jukebox at every table. Similar-but-different, the Oakhurst Diner in Millerton offers an updated version of old-school-diner, with Pho served alongside classic diner plates — perfect for lunch. Other favorite options include farm-fare from McEnroe Farm Market or Big Rock Farms, both of which have grab-and-go or dine-in sandwiches and snacks. You can stock up on local goods at both, too!

For dinners out, it’s a toss-up between Canoe Hill in Millbrook and The Lantern Inn in Wassaic. Canoe Hill offers a little more formal dining service, in a little restaurant with a great vibe, dimly lit by candles and a cozy wood-fire stove. James Beard nominated chef Sara Lukasiewicz serves up a stellar menu of  American classics, complimented with fantastic cocktails, plus a really great happy hour. At the Lantern Inn, expect a more casual/local vibe, but don’t be fooled — the dough comes from a mother starter imported from Sicily. New chef John Dearth comes from Faro in Bushwick, a Michelin starred restaurant, prior to heading Lantern Inn. Their drink menu is awesome as well with lots of local spirits, wines and beers; in warmer months, head to the outdoor area, and grab a spot by the bonfire.