New York isn’t all skyscrapers and concrete jungle. In fact, just across the Hudson River from the Big Apple lies an opportunity to explore the state’s natural scenic beauty, coolest historical landmarks, and culinary delights without the big-city hustle and bustle. If a family vacation to New York is on your clan’s travel bucket list, Dutchess County offers the perfect introduction to the Empire State.

photo: via Four Brothers Drive In Theater


Easily accessible by car, train, boat and air; Dutchess County is home to the cities of Poughkeepsie, Beacon, Amenia, Fishkill and others. The area is packed with opportunities to walk through history, indulge in outdoor recreation, check out art and so much more.

photo: Dutchess Tourism

Walk through History
The history buffs in the family can get their fix visiting and touring historical landmarks from various eras located in the area. The biggest challenge you will face is deciding where to start and which locations to fit in. There are five historic Great Estates that give your family the opportunity to step back in time and take a walk through the past. They include Franklin D. Roosevelt home, Vanderbilt Mansion National Historic Site, Locust Grove Estate and Mount Gulian Historic Site. Each of them offer a combination of tours, galleries, hikes and programs that everyone can enjoy.

Add a little thrill to your historical experience with the Haunted History trail. The trail passes through Dutchess County and includes stops at places like Miss Fanny’s Victorian Party House and Wing’s Castle, both of which are believed to be haunted and offer ghost tours for the brave.

photo: via The Old Rhinebeck

Hit Local Museums
Tiny tots in need of play time will love the Mid-Hudson Children’s Museum where two stories worth of hands-on play exhibits are housed. Highlights include The Children’s Garden, The Science Center’s Wonder Dome and RiverTown—an exhibit area infused with a whole lot of local flavor.

The Old Rhinebeck Aerodrome Museum is packed with antique aircrafts that thrill both young and older aviation fanatics. Along with featuring over 60 vintage aircrafts, antique automobiles and motorcycle, this cool spot hosts airshows! So keep an eye on their website for dates and times.

Art enthusiasts must hit the Dia, located in Beacon. There you will enjoy  rotating temporary exhibitions along with a display of art from the 60s and 70s. This gallery is favored by New York City’s residents who regularly take the train from city to gallery just to delight in its artwork.

photo: Fred Schaeffer

Get Outside
Dutchess County is located in the stunning Hudson Valley landscape where visitors enjoy endless outdoor recreation options. For an unforgettable hike, strap on your hiking boots and head to Beacon Mountain where you’ll find an epic trek that offers big payoffs. This 2.4-mile up and back hike is appropriate for families with hiking experience. It has a well-maintained trail system that takes you by several scenic lookouts. Once you reach the top, you are in for some epic views of the valley and the river. There’s even a fire tower hikers can ascend to get a better look. Don’t be fooled, the experience is not stroll through a park. There are lots of switchbacks (and some stairs). But the work is totally worth it.

If your youngest hikers aren’t quite up for scaling the mountain, no problem, the Walkway Over the Hudson State Historic Park is a great alternative or addition. The path was once a railroad bridge that was built in 1888. Now a walkway suitable for people of all ages, it stretches 1.26 miles over the Hudson River connecting Poughkeepsie (on the east side of the river) to Highland (on the west side). Stroller friendly, families with young children can take in fantastic views of the dazzling Hudson while taking their time crossing the waters.

With the Hudson River running right through the county, there are plenty of options for family waterplay. Little swimmers will get a kick out of the River Pool at Beacon, which is an environmentally friendly partially submerged pool in the Hudson River. It has a permeable floor and sides that create a fence under the water so river water runs through it and little ones get the thrill of swimming in the great Hudson (safely).

photo: Anne L. via yelp


Eat, drink and play at Four Brothers Drive In Theater where you get a taste of the old-school drive-in, but with extra-cool, contemporary flair. Four Brothers doesn’t just offer great bites like burgers, hot dogs and floats with a flick. They provide a next-level family-experience with extras like an onsite petting zoo, hot air balloon rides, face painting and more. And if you get too tired to drive home, you can camp on their property or rent their air stream trailer for the night.

With the Culinary Institute of America located in Dutchess County, you can expect to enjoy some of the best cuisine you’ve ever tasted at local restaurants. For a farm to table dining experience, the Troutbeck in Amenia offers an elevated, but cozy, experience. Breakfast includes fresh-pressed juice and kids and parents alike will melt over the blueberry pancakes. The dinner menu boasts specials like Duck Confit and Black Trumpet Fettuccine. Every dish is delectable and suited for even the pickiest of foodies. For a quick morning bite, hit Café 40 & Co in Poughkeepsie where you can grab an incredible espresso or cup of tea, as well as a bagel, muffin or pick from an array of pastries you can either sit down to eat or take with you to go.

For lunch, head to Lolita’s Pizza in Poughkeepsie where you can nosh on Neapolitan Pizza and pasta. The Short Rib Gnocchi is literally to die for. Baja 328 is Another great lunch or dinner spot. This Southwest grill features mouth-watering fare with dishes that include Seafood Ceviche, Pork Carnitas, Market Fish and tamales. If you are in Beacon, The Roundhouse serves breakfast, lunch and dinner in a beautifully appointed space where you can dine on everything from Brioche French Toast Pain Perdu to a burger to Grass Fed Ribeye.


Dutchess County may not be home to the big city, but your choice in accommodations does not suffer. Located in Amenia, you’ll find the Troutbeck, which was once a private estate and the favored retreat for likes of Ralph Waldo Emerson, Thoreau, Twain, Hemingway, Roosevelt and the giants of the Civil Rights movement. This recently renovated manor house is located on 45 private acres of land where the kids can run and play. Here you will find a babbling creek to relax by along with a walled garden, an area to play games like pool, and a beautiful sitting area with a roaring fireplace. The rooms are quaint and comfy and there is onsite dining and bikes you can check out to explore. A stay at this historical spot gives you an opportunity to experience what it was like to live during a more romantic point in time.

Beacon is home the Roundhouse, another historic building that was transformed into a beautiful, modern boutique hotel. Overlooking a rushing creak that flows into a stunning waterfall, the location is perfect if you desire walkability. It’s located steps away from the Beacon town center where you’ll find plenty of shopping and entertainment. The Roundhouse features well-appointed rooms and onsite dining along with a cozy sitting area where you can relax and chat while enjoying a cocktail.

A weekend or week long escape to Dutchess County, New York gives families an opportunity to see a side of New York that is shockingly underrepresented. Along with getting a good dose of history, you are guaranteed to bond over thrilling and inspiring outings and activities. You’ll end your vacation ready to come back for more.

—Annette Benedetti

Feature photo provided by Four Brothers.


3 Day Itinerary: Visit New York City with Kids 

Niagara to Buffalo: New York Like You’ve Never Seen it

Florida Wellness Vacations for Families