8 Fun Family Travel Options in the Upstate New York

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Looking for a few fun family travel options for America’s East Coast? Next time you’re back east or if you live in one of America’s major New England cities like Boston, Philly, NYC or Providence, then consider exploring the Catskills and other nearby natural gems in upstate New York. We love the region and having grown up in the Adirondacks, are a bit biased, but her mountains are glorious and her lakes are oh so serene.

Here are a few fun family travel activities you can do when you venture north out of the city. Get planning – it’s gorgeous up there.

See an Airshow in Rhinebeck

At the Old Rhinebeck Aerodrome, which is a living museum, they have many examples of airworthy aircraft of the Pioneer Era, World War I and the Golden Age of Aviation between the World Wars.

It is known as America’s first flying museum of antique aircraft and they preserve over 60 vintage aircraft, many antique automobiles and motorcycles, and related memorabilia. Their static display museum is open from May through October and they offer two different airshows each Saturday and Sunday, from mid-June through mid-October.

The town of Rhinebeck is pretty historical for a myriad of reasons and we love it. Be sure to see our Rhinebeck Restaurant Picks. Given its historical past and close vicinity to natural beauty in all directions, having an aviation museum is a perfect addition and is a great option when on a family travel trip.

Not only do they have air shows (season runs from June to October) but you can ride in one too. The stars are the historic airplanes themselves, such as a 1909 Bleriot, the oldest regularly flying airplane in the Western Hemisphere; the Fokker DR-I Triplane, the most famous fighter of World War I; and a precise replica of the Spirit of St. Louis, which was the first aircraft to fly from New York to Paris in 1927. While aircraft rotate on and off the flightline, usually 15-20 are flyable for their shows.

Above photo credits from DutchessTourism.

If you want to ride in a vintage plane, they’ll take you out in a 1929 New Standard D-25 which was designed for passenger hopping by the great flying circuses of the 1920’s and 1930’s. It can carry up to four passengers per flight before and after the weekend airshows as well as on weekdays. They start flying at 10 AM and continue to dusk.

Above photo credit: Old Rhinebeck Aerodome.

Make Your Own Pizza at Stony Creek Farmstead

We discovered an organic farm gem called Stony Creek Farmstead on the outskirts of a town called Walton.  The farm is owned and worked by three generations of the Marsiglio family and they have “make your own pizza” on Saturday nights starting at 6 pm during warmer months.

Their charming farmstead is nestled deep in the Catskills surrounded by winding country roads that take you past grazing cattle, rolling fields and century-old barns.

The current owners Kate and Dan started growing meat, eggs, and vegetables for sale now more than ten years ago, all of which are free-range and beyond organic and they offer best pasturing practices for all of their animals. Their cows and sheep are 100% grass fed and their pigs and poultry supplement their pasture diets with locally grown certified organic grains – bravo!

It’s a great thing to do with kids, because it shows them where food is sourced from and how to make their own food. It’s donation only and everyone shares what they make. In other words, your pizza may be partially eaten by someone else and you will likely sample someone else’s pizza. They have a couple of large salad bowls to accompany all those carbs.

They roll the dough for you and you top your own pie. People bring soda, beer and wine to go with their meals and kids run around in the fields nearby and play.

Someone mans the oven and you watch while your pizza pie bakes – how cool is that?

The result? Delicious Italian magic of course.

You can also stay on the farm, but it’s fairly rustic — in other words, no electricity. But, it’s a great way to connect with nature and teach your kids the value of living among the earth. Kids will be introduced to beef cows, a flock of sheep, heritage breed pigs, and innumerable chickens.

Above photo credit: Stony Creek Farmstead

The accommodation is a rustic platform tent with canopied ceilings and canvas walls. The tents have a wooden floor underfoot and there’s a fully equipped kitchen with a wood cook stove and essential utensils for cooking.

Each tent includes a cabinet bed for concealed midday naps if you’re traveling with kids, as well as a set of bunk beds and a separate room with King size berth. A small water closet conceals a flush toilet and a short stroll across a foot bridge brings you to the industrial open air shower house, with four stalls, two family size and two singles.

You’ll be off the grid here but that’s precisely what it’s about — experiencing farm life, getting close to nature, and walking in their beautiful hills. They have a crystal clear pond nearby and if it rains, there’s cards and board games.

Canoeing & Kayacking with Al

Okay, so you don’t really go canoeing with a man named Al, but Al does own a motel and sports store in Delaware County’s Downsville New York.

The sports store itself is charming and you can get what you need for fishing as well as rent canoes and kayaks for use down the Delaware River nearby. Al also finds some great wood gifts, from furniture, Adirondack-like chairs and bird houses to planters and items for kids. They even sell local honey which we bought before we left.

Canoeing (or kayaking) from this part of the Delaware River takes you past pristine forests and you can even get off on the way if you’d like and hike to a hidden lake. We passed a man fly fishing on our way who was standing in the middle of the river, whereas we saw a couple others fish from shore.

Located at the foot of the Pepacton Reservoir on the East Branch of the Delaware River on Routes 30 & 206, Al’s Sports will set you up with whatever you need — we opted for two canoes. You can get the boats for two hours or four hours depending on how long you want to be on the water.

Additionally, they specialize in trophy trout fishing for the reservoir and the surrounding rivers and lakes in the Catskills and they are also an authorized agent for issuance of NY State Hunting and Fishing licenses. Our journey down the river and under two bridges was spectacular – a two thumbs up choice!

Re-Enact the Civil War

We personally love history over here and wish we could cover the historical aspects of places we visit more than we do. It was an accident that we fell upon Delaware County’s living history exhibit and Civil War Battlefield Reenactments, which is put on by the Delaware County Historical Association.

Below, is where they set up the battlefield. On the premises, they set up dueling canons, a fun shop, a museum, civil war camps, a blacksmith and an area for kids activities in what they referred to as the Toll House. Kids are able to learn about Civil War horses and discover some of the period’s most notorious figures, interact with reenactors and learn to eat like the soldiers did during the war.

Reenactments included the Battle of Honey Hill, Battle of Fredericksburg and the most famous one, the Battle of Gettysburg, which was led by General Pickett from Virginia. It’s most known because of its historical impact and the fact that it resulted in 6,000 Confederate casualties.

Breathtaking Country Drives

The Catskills encompasses many counties as you venture north from the Big Apple and each one we went through had breathtaking drives with plenty of green pastures, trees and hills. Unlike the drought we’ve been experiencing in California, where the hills are yellow and dry, the land throughout the Catskills was lush and green.

The Car You Take on a Family Trip Matters

On this particular trip, we drove a Buick Envision, one of the smaller luxury Buick cars we’ve tested out over the past couple of years. I LOVE this car. We experienced the Buick Enclave back in October and the Buick LaCrosse last winter — we really loved those heated seats. We also tested out the previous year’s LaCrosse as well. In other words, we’re Buick fans.

The Buick Envision is considered a small luxury SUV car so it didn’t have as much space for luggage as the Enclave and LaCrosse, however it was much easier to navigate and park in small places.

Why so great for family travel? Imagine the hours we put on during these country drives. If you’ve got kids in tow, you know that they’re always antsy and the ride is never short enough. The Envision has Apple Car Play compatibility so the kids could access Apple Music, Maps, make phone calls, and send messages. It also has a 4G LTE Wi-Fi Hotspot which was not only great for the kids to watch movies and chat with their friends, but it helped us navigate through more remote areas when Verizon didn’t work on our phones.

It’s also a super safe car and it has HiPer Strut front suspension, which equates to more more responsive steering, improved cornering and reduced noise and vibration. Noise is also a consideration when you’re traveling with kids and this auto gem has QuietTuning technology and hands-free power liftgate.

From old red barns and churches to breathtaking fields and rivers, we drove past them in that Buick.

We also drove through small towns, such as East Meredith — we stayed in yurts here, Downsville, Walton, Delhi, Oneonta, Bloomville, Marlboro, Ellenville, Hobart, Fraser, Treadwell, Prattsville, Sidney, Stamford, Windsor, New Berlin as well as Tarrytown, Red Hook, Milton — we stayed in a historical inn and farm — and Rhinebeck further south, where we stayed in America’s oldest inn.

There were plenty of antique stores, coffee shops and cafes as well as home town cooking along the way. A few routes in the Catskills we didn’t take and are further away from the region we explored on this trip include the following:

  • Route 55: Neversink to Liberty: This takes you past the deep blue waters of the Neversink Reservoir before reaching the town of Neversink which has a river of the same name — it is thought to be the birthplace of American fly fishing.
  • Old Route 28 to 212: Phoenicia to Woodstock: Stop in Mt Tremper and see live music at Bearsville Theater.
  • Shawangunk Mountains Scenic Byway: 82 Miles: Travel through the  Shawangunk Mountains, one of New York State’s most famous rock climbing destinations, which has tons of hiking trails, historic sites and boutique shopping. Artists love this route.
  • The Mountain Cloves Scenic Byway: 41 Miles: This route takes you through the  Northern Catskill Mountains, which has attracted centuries of artists and authors. There are plenty of stunning vistas and verdant valleys to take in along the way.

There’s also Shawangunk  Grasslands National Wildlife Refuge, Mohonk Mountain House and the Hugenot Street National Historic Landmark.

There are lots of waterfalls in the Catskills as well — you can hike to Kaaterskill Falls, the highest cascading waterfall in New York State, the former site of the Catskill Mountain House and Sunset Rock. You can ski in Hunter Mountain during the winter, but during warmer months, they offer the longest, highest and fastest zipline canopy tour in North America (and the second largest in the world).

Nature and Animals

We stayed at the lovely Buttermilk Falls Inn, on the outskirts of Milton (technically still Milton). This farm had so much beauty that we took in their precious animals, flowers and nature on the premises. You’ll find plenty of the same everywhere you turn – gorgeous trees, flowers, rivers and breathtaking views.  I’ll let the photos take you on a magical journey.


Stay in a Yurt & Walk a Labrynth

We stayed in a yurt in the rural area surrounding Meredith, which is about a 3.5 hour drive north from the city. Our article and review of the property says it all, so be sure to read it if you have an interest in staying in one, don’t know what one is, or are simply curious.


It’s a great way to get your kids out in nature and be close to trees, fields and places they can run free. Harmony Hill Retreat Center however makes a great escape for artists, authors, solo travelers and couples as well and tends to attract more couples than families.

They had a labrynth on the premises as well, which is often used in modern circles for spiritual purposes and even healing. This one was particularly special and I’d recommend walking it with your children, explaining the significance and history behind them.


Dance & Play Pool in a Castle on the Delaware

When we headed south from our yurt to make pizza (as noted above), we drove through the town of Walton, which suddenly surprised us with a castle in the center of town — yes really.

The owner is Turkish born Mustafa Sav who is also the chef. He was a student in the five year culinary program at the Klessheim International Hotel and Restaurant Management School in Salzburg. So in other words, he knows how to cook.

The house was built in 1885 by William B. Ogden for a niece of Arthur W. North, both pioneering families and the first settlers in the area. It once served as an old Armory until Mustafa bought it in 2006.

Below, before the sun set. He’s now owned the property for more than ten years and there’s been many renovations since. The building has seen many changes and served many purposes over the years. The Old Armory reopened its great doors as “The Castle On The Delaware” in 2013.

The restoration of the building is an ongoing process and steps are taken to preserve this treasured historical building as closely as possible to its original state. The main floor has been beautifully restored and is now a restaurant for locals and visitors alike.

We ate elsewhere but was told to come back for live music and of course, we encouraged the kids to dance. Instead, we played a few hours of Foosball (they have two) and pool. There’s also a dart board but only one dart, so we used the gaming tables for most of the night.

Worth noting is that there are also several stand up pianos that separate the bar and game area from the restaurant and dance floor. They also do catering events as well and the wife of the owner is Ukranian and incredibly charming.


Note: we were hosted by Harmony Hill and Buttermilk Falls Inn but were not told what to write or influenced in any way. Buick also loaned us a car for our trip. All opinions expressed are entirely my own.

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