Blake Walsh

20 Best Things to Do in Middletown, NY

  • Published 2022/08/12

Set in the beautiful Hudson Valley, the unassuming town of Middletown, New York has many attractions and destinations for the young and old alike.

It’s part of the vibrant Orange County, and it once served as the home for employees who worked in Metropolitan New York.

However, many have left after the city mandated workers to reside within its limits, leaving Middletown with a small population that still continues its traditions until today.

This heritage is primarily agricultural in nature, with a few historical practices and activities that make the town a true New York community.

There are also natural attractions typical of the Hudson Valley, and you’re welcome to visit and appreciate the majesty of these places.

So for your next vacation, why not spend a weekend here?

Here are the 15 best things to do in Middletown, NY:

Catch a Show at Paramount Theatre

Outside View of Paramount Theatre

Brian Logan Photography /

Middletown is filled with historic churches, buildings, and other establishments, and one of these is the magnificent Paramount Theater.

Listed under the National Register of Historic Places, this building has been around since 1930 and has a distinct Art Deco architecture.

It was closed in the 1970s because of competition against theater chains, but the Arts Council Of Orange County revived it into a performance art center.

The theater holds various events such as dance recitals, summer camps, art exhibits, and film features.

It has maintained its status as an important part of the Middletown community, attracting many of its residents for the exciting and engaging events.

You’re welcome to visit too!

Check out their calendar so that you can schedule your trip around an event that you want to attend.

Bounce Without Inhibitions at Urban Air Trampoline and Adventure Park

Urban Air Trampoline and Adventure Park is a favorite destination for those who want to try exhilarating activities while staying indoors.

This fun family attraction offers lots of activities that are great for kids and the kids at heart.

Of course, the most prominent attraction here is the high-performance trampolines where you can bounce around all day or to your heart’s desire.

However, there are also other games and amenities like dodgeball arenas, rock climbing walls, rope courses, and climbing hills.

Adults can also enjoy the fitness classes that let them stay active and in shape.

What’s best about this attraction is that the facility is kept clean every day to ensure the safety and wellness of every visitor.

It’s also located inside Crystal Run Mall, so you can easily visit other stalls and shops when you’re done playing with your family.

Have a Fun Family Day at Fancher-Davidge Park

Fancher-Davidge Park is a well-known destination that attracts locals and visitors alike.

The lush grounds, a large fishing pond, and shady wooded areas all create a family-friendly and scenic outdoor facility.

You’re welcome to explore the forested trails and take a moment to appreciate the beauty of your surroundings.

If you’re bringing kids, let them have fun all day and socialize with other children on the park’s play structures or splash pad.

For those who find fishing a relaxing experience, bring your own hook and line and try catching some of the freshwater creatures swimming in the depths of the pond.

You can also try more active sports like disc golf or swimming, as the park has its own lifeguarded swimming pool open to the public.

View the Sceneries of Middletown Reservoir Trails

Middletown Reservoir Trails is a newly opened facility open for adventurers and nature lovers.

It’s essentially a set of trails that will bring you to the forests surrounding Monhegan and Highland Lakes, covering an area of 1250 acres.

The different routes have varying degrees of difficulty, with some more strenuous or wilder than the others.

Depending on the terrain, you can try hiking, jogging, or running through these routes.

You will see the beautiful forests irrigated by these bodies of water, which also supply the drinking needs of Middletown’s residents.

And since the place is relatively underdeveloped, life still abounds within the forest undergrowth and canopy.

So while exploring, try spotting foxes, birds, deer, and even black bears.

Just be sure to keep your distance for your safety.

Explore Highland Lakes State Park

Waters of Highland Lakes State Park

weskaniaphotography from Middletown, NY, USA, CC BY 2.0, via Wikimedia Commons

With more than 3,000 acres of underdeveloped forests and lakes, Highland Lakes State Park is the largest facility of its kind under the care of the Palisades Interstate Park Commission.

This is the perfect place for those who want to commune with nature and leave their busy lives behind.

Because of its relative isolation and lack of modern amenities, it has maintained a pristine and undisturbed state.

So don’t expect toilets or flowing water here.

There are many opportunities for self-sustained camping and exploration through the thick woods and remote trails that wind through the park.

The lakes are also perfect for fishing and kayaking for those who are feeling adventurous.

After securing a permit, you can also try horseback riding along the wider and more well-paved trails.

Play a Few Rounds at Wallkill Golf Club

If you are a golfing enthusiast, then make sure to make a stopover at Middletown’s premier public golf course.

With its scenic surroundings, well-maintained fairways and greens, and well-planned layout, Wallkill Golf Club guarantees a solid gameplay for beginners and professionals alike.

It’s also relatively isolated from the more developed parts of the city, so you’ll only hear the sound of swaying trees and the babbling streams that also serve as water hazards.

While some parts are quite challenging in the 18-hole course, the overall gameplay is relatively easy, thanks to the flat and stable terrain.

In fact, qualifying games for national amateur tournaments have been played here.

It’s a testament to how the course has become an integral part of the New York golfing scene.

Spot Native Birds at Moonbeams Preserve

Moonbeams Preserve is a hidden gem for nature lovers and bird watchers, located east of Wallkill Golf Club and far from the Middletown city proper.

So you can expect an isolated and quiet nature destination that is perfect for hiking and exploring.

While trekking the 1.3-kilometer trail, you’ll encounter small streams, meadows, and forested areas with some traces of human habitation.

It’s a relatively easy hike that’s great for all skill levels.

Along the way, you’ll see habitats like fields and wetlands that serve as homes for wildlife native to the Hudson Valley.

Birds are the most common species, including waterfowl, birds of prey, and everything in between.

So make sure to bring your binoculars or cameras if you want to see them as they flit about in between branches.

Stay Awhile at Circleville Park

Circleville Park is the best destination for water-related activities during your stay at Middletown.

It’s a large attraction with 700 acres of space that you are free to roam and explore with friends and family.

Right in the middle is a seven-acre lake where you can try activities like kayaking, swimming, and riding on paddle boats.

It’s surrounded by an interrupted tree line mirrored on the lake’s clear surface, which adds to the majestic scenery of the surroundings.

Fishing is encouraged, and you’re welcome to spend all day along the shores or on a small boat trying to catch the creatures swimming in the depths.

But if that’s not your preferred activity, you can simply stay under the shady trees and enjoy the lush greenery and quiet ambiance of the park.

You can also have a picnic with your family in one of the pavilions or the designated grilling spots.

Reach the Sky With Above the Clouds Hot Air Balloon Rides

For those feeling adventurous, why not hop on a hot-air balloon and see Hudson Valley from a bird’s-eye view?

Above the Clouds Hot Air Balloon Rides offers exhilarating trips that bring you towards the clouds—an unforgettable and thrilling experience that you shouldn’t miss.

The owners have been flying for more than 34 years and have continued to develop new safety measures to ensure that every passenger has an enjoyable and secure ride.

So you can have peace of mind knowing that you’re flying with professionals.

The views atop the baskets are quite magical, especially during fall when the foliage changes and there’s a mix of orange and green hues all around you.

And with the relatively even terrain of southern New York, the scenery goes on and on for miles without being interrupted by mountains.

The best time to try the balloon rides is during summer and early fall when the weather is calmer and the skies are clearer.

So schedule your trip around these months if you are planning to take to the skies.

Watch a Car Race at Orange County Fair Speedway

A Car at Orange County Fair Speedway

Bruce Alan Bennett /

While the Orange County Fair is only a once-a-year activity, the Orange County Fair Speedway has events every week!

So if you’re a racecar enthusiast or just looking for a thrilling show while staying at Middletown, then this place is just for you.

In the past, it was the site for horse races, which was the typical entertainment during the 1800s.

A Car at Orange County Fair Speedway

Bruce Alan Bennett /

But today, the one-kilometer dirt speedway holds exciting stock car races and rambunctious demolitions derbies.

There’s also a recently built motocross track, which only added to fun events that you can watch while visiting.

So bring the family over and buy the best seats!

Roaring along with the crowds and the noisy cars as they race towards the finishing line is an experience you won’t forget!

Pitstop at Orange County Fair Speedway

Bruce Alan Bennett /

Drink Cool Beverages at Clemson Bros. Brewery

The perfect way to cap off a whole day’s worth of touring is a mug of refreshing beer at Clemson Bros. Brewery.

Set in a historic building, this microbrewery is a Middletown institution established by the Clemsons, an old family of the city.

Using traditional ingredients and modern innovations, the owners create some of the finest alcoholic beverages around.

You can try craft beer of various flavors, fruity drinks, and seasonal offerings that are sought-after by locals and visitors alike.

There’s also a menu consisting of American staples that perfectly complement every sip of the delicious beers offered here.

Before you leave, don’t forget to bring home a pack or a few cans to drink during special occasions or after long days.

Cruise the Gentle Wallkill River

The waters of Wallkill River

ShawnCarstensen /

Wallkill River is one of the chief tributaries of the Hudson River, and segments of this waterway pass through the city of Middletown.

There are many charters and small businesses in the city that offer tours and charters to the river.

So if you’re planning to explore this scenic body of water, find the ones that offer kayak or canoe tours, as these are the best modes of transport for sightseeing.

Cruising the gentle currents will bring you to the attraction’s many unique habitats, including wet meadows, floodplain forests, and swampy areas.

These diverse locations allow for a wide range of animals and plant species to flourish along its banks.

So keep an eye out for colorful butterflies, curious river mammals, and some migratory bird species that call this place home.

There are also segments with more turbulent waters, which you can either avoid or plow through if you want some thrill along the way.

Join the Fun at Orange County Fair

Having been around since the turn of the 19th century, the Orange County Fair is considered to be New York’s oldest fair!

It all started more than one hundred years ago with the farmers of Hudson Valley wanting to sell their agricultural products to the general populace.

Over time, it has evolved into this huge gathering that includes car races, circus and carnivals, live music, firework displays, and more!

One of the most anticipated events here is the Banana Derby, where cute Capuchin monkeys ride dogs like jockeys ride horses.

There’s also a petting zoo with many adorable farm animals just waiting for friendly hugs and pets.

Of course, live music is the most anticipated event during the show, mostly because of the high-caliber artists that headline the event.

Some of these acts include Boyz II Men, Bob Dylan, Aerosmith, and Guns N’ Roses,

To catch all these, simply buy a ticket that will give you unlimited access to rides and events!

Order a Craft Beer at Equilibrium Brewery

Independently operated Equilibrium Brewery is a craft brewery featuring a taproom, beer garden, Grilling program, and retail area.

Based on scientific concepts learned at MIT, a passion for local beer, and an appreciation of community, their mission is to produce the greatest beer in the industry.

They create the beverages they enjoy drinking and serve them to their customers.

The brewery makes sure to maximize and regulate the proper distribution of flavor-active molecules in each glass; their beers are brewed according to the “Mass Balance Brewing” approach, particularly focused on the sources and sinks of various tastes.

They believe the appropriate craft beer may elevate average experiences to remarkable ones.

Read a Book and Gain Knowledge at Thrall Library

Exterior of Thrall Library

Daniel Case, CC BY-SA 3.0, via Wikimedia Commons

Would you want to go to a location where you can just relax and read a book?

There is a public library called Thrall Library on Depot Street in Middletown.

Thrall Library is the ideal location for you to read a wide variety of books on many themes, such as politics, economics, and cultural issues.

You may also read books here on social and religious events.

Exterior of Thrall Library from across the street

AlexiusHoratius, CC BY-SA 4.0, via Wikimedia Commons

You will be able to discover the illustrious past of Middletown and the United States in general.

The library provides a wide selection of publications, including children’s books and books about current events in the country.

Simply by stopping by and taking a few minutes at the Thrall Library, you will learn something new.

Go on a Shopping Spree at Galleria at Crystal Run

Exterior of Galleria at Crystal Run

Melissa Blair /

The Galleria at Crystal Run offers ideal weather throughout the year by bringing together the major brands you’re looking for with a wide variety of niche and family-run retailers all under one roof.

With more than 100 businesses to pick from, you can shop like there’s no limit.

The Galleria at Crystal Run has everything you may want, including furniture, clothing, and accessories.

Foodcourt in Galleria at Crystal Run

Daniel Case, CC BY-SA 4.0, via Wikimedia Commons

You may find various places to eat at The Galleria at Crystal Run, including sit-down restaurants, a food court, and snacks.

These selections range from traditional American cuisine to delicacies from the Far East.

Numerous shopping, eating, and entertainment establishments within The Galleria at Crystal Run offer annual specials and promotions.

Dine at DeStefano’s Olde Erie

After a long and stressful week, are you feeling worn out and searching for a spot to have a drink to unwind?

DeStefano’s Olde Erie serves the most sumptuous meals in the area and an ambiance to complement them.

The food at DeStefano’s Olde Erie is bursting with flavor; their ingredients are always fresh, and their recipes are traditional and authentic.

This elegant restaurant serves classic American and Italian dishes, including exquisite spaghetti, juicy steak, and delicious hamburgers.

When you’re nearby in the area, drop by DeStefano’s Olde Erie and partake in a favorite old-time restaurant.

Enjoy Live Entertainment at the Switch Inn

Neon sign of the Switch Inn

Wirestock Creators /

The Switch Inn is more than simply a conventional establishment.

It always has events and is a terrific location for evening drinks at the bar, a get-together with pals, or a drink with your loved other on their outside deck.

The Switch Inn offers something for everyone, whether you eat in or take away.

They provide fantastic live entertainment, themed parties, sports packages, karaoke, and much more.

They also have delightfully inventive seasonal cuisines in addition to terrific weekly discounts.

Other Things to Do Nearby

After your tour of Middletown, why not visit these other attractions in the vicinity?

Commune With Nature at Orange County Arboretum

The grounds of Orange County Arboretum

Brian Logan Photography /

Northeast of Middletown lies an attraction that perfectly fuses modernity and nature: the Orange County Arboretum.

Along with perfectly landscaped gardens, magnificent terraces, and bubbling fountains, you’d find a myriad of plant species found in the Hudson Valley and surrounding regions.

It’s a great place to learn about these trees and flowers and appreciate their beauty as they bloom or change foliage.

Unique water fountain at Orange County Arboretum

Brian Logan Photography /

Go Backcountry Camping at Stewart State Forest

A Sign in Stewart State Forest

Daniel Case, CC BY-SA 3.0, via Wikimedia Commons

Further north is another nature-related getaway that promises a rewarding experience for the adventurous and daring.

Stewart State Forest is one of the most popular destinations on this side of New England, especially for hiking, camping, and hunting.

You’re welcome to explore more than 6,700 acres of wetlands, hills and meadows, and waterways that create unique habitats for a wide range of wildlife.

Great swamp at Stewart State Forest

Mad Hare Imagery /

Final Thoughts

From long-standing fairs to newly developed trails, from thrilling balloon rides to exciting races, the attractions of Middletown contrast with one another.

But that’s what makes it an excellent destination for every preference!

So when planning your vacation to this charming town, check out this list and include the best spots to your itinerary.

© All rights reserved.