Dutchess County is a no brainer for a family weekend getaway. It’s a quick two hour drive from New York City and parts of New Jersey and Connecticut, so with a reasonably early start you can make the most of your short vacation. And with a wealth of attractions from fall apple-picking and easy hikes to historic mansions and locavore food, there is plenty to please both kids and parents over a two-day stay. 

Metro-North sometimes partners with Visit Dutchess and area attractions to combine train and shuttle service for day trips. If you’re staying a weekend though, it’s better to have a car. You can also bring bikes on Metro-North but be sure to apply for a permit first. 

Consider this your Dutchess sampler: It’s enough historic and cultural sites, kids’ activities and outdoor opportunities to fill several weekends. Scroll to the end for dining and hotel ideas and start planning your next mini-vacation (or two). (Read more about the Hudson Valley, the Catskills, and a Romantic weekend here.)

Easy HudsonValley Weekend With Kids

American History

Eleanor roosevelt's typewriter at the fdr museum in duchess county
Fdr's car at his library in dutchess county
History at Hyde Park

• I love Hyde Park and have visited both with and without my now 8YO. The estate visit can include Franklin Roosevelt’s lifetime home, Eleanor Roosevelt’s separate estate, Top Cottage (FDR’s hideaway), the Roosevelt Library and a vast amount of land that you can roam for free.

The homes have to seen with a guide, and you would want one anyway for the stories they can provide. 

The tour of FDR’s house was short enough and featured enough quirky items to keep Tiny Traveler from being bored.

She’s too young to understand why I adore Eleanor Roosevelt. While I found the guide’s stories about this First Lady’s life and home amusing and interesting, she was a little lost.  

We didn’t do Top Cottage together. But you can read about why it’s my favorite part of Hyde Park.

• Kids with some knowledge of 20th century American history will get the most out of the FDR library. But it’s big and interactive enough that most kids 8 and up will find something to engage them. 

Tiny Traveler was most interested in FDR’s old family photos, specially rigged car and cluttered White House desk. Eleanor’s manual typewriter fascinated her. She stared at it for a long time before asking, “how does it work?” 

The living room of the vanderbilt mansion in dutchess county

The library has a Junior Secret Service program and the house has a Junior Park Ranger program. Ask for both when you buy your tickets at the visitors’ center.

The Gilded Age at the Vanderbilt Mansion 

• The opulent Vanderbilt Mansion (top), which was built to let the world know just how much money the family had, is a nice contrast to Hyde Park, which exemplifies discreet “old money.”

Tiny Traveler observed the bedrooms modeled on Versaille, the built-to-impress public rooms and oh-so-rich studies and lounges and one-by-one declared them all “ugly.” The Park Ranger talk about the family and this “modest” weekend house is informative, well-done, and short enough for kids to handle it.

Note: Like Hyde Park, this house has extensive grounds and beautiful gardens that are open to the public; It’s a particulary good place to ramble around with kids who might have excess energy after all these house tours.

Outdoor Fun

• The Walkway over the Hudson is a repurposed railroad bridge that’s one mile long. It’s a nice easy walk with fabulous river views.

Walkway over the hudson extends from dutchess county

Kids can bring scooters and it’s stroller friendly. With tweens and teens you can bring bikes and connect to trails on either side..

A park below it on the Dutchess side offers the children’s museum, a playground and the Ice House Café, with great river views in warm weather.

Kid Fun

Rainy Day Idea

• At age 8 Tiny Traveler is nearly too old for the smallish, well-maintained Mid-Hudson Children’s Museum, below the Walkway, but she still enjoyed it.

In an hour we were able to sample almost everything she wanted to, and two hours would have been plenty of time to do it all. When she was smaller she would have stayed for hours in the pretend-play areas on the first floor.

Summer Fun

• Splashdown Beach water park is on our to-do list for the summer. It’s bigger than it looks from the outside, Mommy Poppins gives it a good review and on a hot summer weekend it’s a good reward for kids (and parents) who behaved well on all those park-ranger tours.

Playground Time

Beacon waterfront playground in dutchess county

• On our two-day Dutchess Sojourn we found 3 playgrounds. None are super new, but all were large and in good shape and kept energetic Traveler happy.

One, at the opposite end of the waterfront from the Estuary Steward’s dock in Beacon, provided shade and nice river views for me while she played (right).

A second was in Poughkeepsie’s waterfront park below the Walkway, at the opposite end from the kid’s museum (there is parking at either end, too, if you want to do one but not the other).

The last was tucked away in Rhinebeck. Head west on market Street and less than a half mile from Mill Street you’ll turn left for the Starr Library and Starr Park with its cool climbing structures (but no shade).

Dutchess Culture:

Old Factory, Modern Art

• DIA: Beacon is a modern art museum in a former box-printing factory. The high ceilings and large spaces make it ideal for larger scale and three-dimensional pieces of art.

They also make it a kid-friendly gallery space. If your child is as candid as mine, expect the post 1960s art to elicit surprising and sometimes funny reactions.

Note: The museum is closed Tuesdays and Wednesdays and in the winter on Thursday as well.

A River Island

Bannerman island in dutchess county

• I was lucky enough to go on a press tour of Bannerman’s Island this spring.  It’s an interesting and ambitious project. The island is home to the former Bannerman Munitions warehouse, which now resembles a large ruined castle. Owner Frank Bannerman also had a home on the island, a smaller now-ruined castle.

The island is still rough around the edges, but it’s a work in progress worth keeping your eye on. It hosts a diverse series of tours, performances and art installations that change a bit each summer, some geared toward families and others family friendly. Money raised goes toward restorations and upgrades.

Note: To get to the island you take the RV Estuary Steward, which leaves from a dock just below the Beacon Metro North Station. Event ticket prices include the boat trip.

On select days you can book a boat trip and guided tour or boat-trip and self-guided walk. Three local companies offer kayak tours around the island.

Note, too: The island has no running water or electricity. They’re working on eco-friendly toilets but in the mean time you’ll have to deal with the portable variety.

Searching For the Red Baron

A german wwi fighter plane at the rhinebeck aerodrome

• On yet another weekend we spent an afternoon at the Old Rhinebeck Aerodome. It’s vintage-plane air shows draw people from all over on weekends; during the week the museum is open for walking around and looking at early 20th century planes and automobiles. 

Rich and I enjoyed getting close-up views of the WWI fighter planes and other vintage models, and we were highly entertained by the pilots acrobats and chases.

Despite her affection for Snoopy’s antics as a WWI flying ace, Tiny Traveler was intrigued by the old planes for all of about 20 minutes. Then she was mostly interested in the hot dogs, ice cream (both good) and gift shop. In my book planes are high on the list of things kids are supposed to find exciting but don’t. 

Dutchess Dining:

 Beacon and Rhinebeck are walkable towns that offer plenty of dining options along their main streets.

• Terrapin in Rhinebeck is creative and casual with a focus on local and organic. It has a good kids’ menu. The casual café/bar is ideal with kids (save the dining room for date night). City dwellers will know the Bread Alone bakery from its green market stalls. In Rhinebeck try it’s café for sandwiches and breakfast items like French toast, which feature its rustic breads.

• In Beacon we had freshly made and really cheap chicken and waffles at the no-frills BJs Soul Food on main street. On another visit we had terrific sweet and savory crepes at Royal Crepes.

Places to Stay:

We spent a night at the recently renovated *Holiday Inn Express just south of Poughkeepsie, a predictable but reliable option with kids. It’s right on Route 9, which makes it super convenient to get to everything you want to see. The free breakfast had ample and healthy choices and it has an outdoor pool in summer. They also give out chocolate chip cookies in the afternoon.

We’ve also stayed in the *Pougkeepsie Grand Hotel, right in Poughkeepsie. It’s close to some dining, the Walkway, the children’s museum and Bardavon, a picturesque theater that attracts good music acts and family shows. Rooms on the higher floors have river views. And both parking and breakfast were included.

The Inn at Bellefield, a Marriott Residence Inn, is scheduled to open near the Culinary Institute of America in late 2019.

Rhinebeck has the historic Beekman Arms, with surprisingly good off-season rates, breakfast and high 4-post beds your kids will love. There’s plenty to walk to right in town.

You’ll find other affordable chains around Poughkeepsie to and independent inns and B&Bs around Rhinebeck

Pin it for later!

*We were guests of Dutchess Tourism at the Holiday Inn Express and Poughkeepsie Grand Hotel. Dutchess Tourism also hosted our visits to Hyde Park, the Vanderbilt Mansion and Bannerman Island. Other activities we did on our own. We promise no particular coverage in exchange for sponsorships and our opinions are always our own. 

*Select photos are courtesy of the National Archives, Walkway Over the Hudson and Royal Crepes. 

This blog was part of Weekend Travel Inspiration with 

• AlbomAdventures
• ContentedTraveller 
• TheCrowdedPlanet
• Malaysian Meanders
• ReflectionsOnRoute 
• Safari254

Previous post

How To Explore The Florida Keys With Kids

Next post

Best Things To Eat On Cape Cod With Kids