15 Best Things To Do In Middletown, New York - Updated 2021

things to do in middletown new york
Stephen
Stephen
Updated

Middletown is a city in Orange County, New York, strategically located near the Wallkill River and the foothills of the Shawangunk Mountains. It lies magnificently between Port Jervis and Newburgh. It boasts a variety of iconic attractions that bring people from all over the globe. The town will tempt you with things to do that you will find hard to ignore. From going for social events and dining at independent restaurants to exploring art, learning about local history and touring parks, Middletown has a lot of fun things to offer that will keep you entertained. Stay at the top Airbnb vacation rentals in town, and read on to find out more about things to do in Middletown, New York.

1. Stroll through Highland Lakes State Park

Highland Lakes State Park
Source: Photo by Wikimedia Commons user weskaniaphotography used under CC BY 2.0

Highland Lakes State Park is a vast piece of land more than 3,000 acres (1214 hectares) of undeveloped woods and lakes strategically located along Tamms Road, in Orange County. If you love participating in a breathtaking adventure, then you should be thinking of paying this park a visit. Take your loved one and head out on a romantic getaway in the thicket of the trees and bushes in the park. The presence of a lake and nature trails makes the park a suitable place for activities such as hiking, fishing, horseback riding, and even model aircraft flying. Visit the park and enjoy natural fun.

Highland Lakes State Park

Address: 55-223 Tamms Rd, Middletown, NY 10941, USA

Website: Highland Lakes State Park

2. Watch a movie at Paramount Theatre

Paramount Theatre, Middletown, NY
Source: Photo by Wikimedia Commons user Daniel Case used under CC BY-SA 3.0

Among the many iconic and historical attractions and cultural heritages of Middletown, the historic Paramount Theatre remains one of its special gems. It’s one of the best places to go in Middletown, NY. This iconic theatre demonstrates a perfect example of the Art Deco styling that was famous during the 1930s. You can take your camera with you if you would love to take some photos for memories. It has been a place where the local residents have always trickled down to watch movies. From the older generations through to Millennials, people have been enjoying a wide variety of films and performances. Going there to watch a movie might be the best way to spend your evening in Middletown.

Paramount Theatre

Address: 17 South St, Middletown, NY 10940, USA

Website: Paramount Theatre

3. Take a tour of Thrall Library

Thrall Library, Middletown, NY
Source: Photo by Wikimedia Commons user Daniel Case used under CC BY-SA 3.0

Thrall Library is a public library that is situated on Depot Street in Middletown. Do you love reading books? This is the perfect place where you will be able to read a wide selection of books on different topics including politics, economic and cultural matters, social and religious happenings too. You will be able to learn about the prestigious history of Middletown and of America at large. The library has all kinds of books including kids’ books and materials on the current matters in the country. You will get to learn just by visiting the Thrall Library and spending some time there.

Thrall Library

Address: 11 Depot St, Middletown, NY 10940, USA

Website: Thrall Library

Opening hours: Mon - Thu: 9am - 8pm; Fri: 9am - 6pm; Sat: 10am - 5pm; Sun: 1pm - 5pm

4. Shop at Galleria at Crystal Run

Galleria at Crystal Run interior
Source: Photo by Wikimedia Commons user Daniel Case used under CC BY-SA 3.0

Galleria at Crystal Run is a shopping center and actually the second largest shopping mall in New York’s Hudson Valley region. This mall is strategically located in the town of Wallkill, New York. From fashion boutiques and art galleries to food courts and restaurants, the mall serves as the perfect one-stop shopping destination. There are a lot of social and entertainment joints in the mall providing all forms of entertainment including nightlife. You can shop for anything there including for birthday parties, kids’ stuff and even souvenirs in the many art galleries. Hop into one of the restaurants and enjoy special delicacies as you continue shopping.

Galleria at Crystal Run

Address: 1 Galleria Dr, Middletown, NY 10941, USA

Website: Galleria at Crystal Run

Opening hours: Mon - Sat: 10am - 9:30pm; Sun: 11am - 6pm

5. Sharpen your problem-solving skills at Escape The Mystery Room

Escape Room Mystery
Source: Pixabay

Photo is only for illustrative purposes

Located in the Galleria at Crystal Run on Galleria Drive, Middletown, escape room center presents you with an opportunity to be a real-life detective. This is a good opportunity to take your family out and have fun together solving mysteries and puzzles. Or it could be that you are planning a social event with friends or a team building activity with colleagues, whatever it is, even a party, Escape the Mystery Room is the perfect place to head to. This is an ideal place where you get the chance to engage in mentally challenging exercises and social activities that bring fun and sharpen your brains.

Escape The Mystery Room

Address: 1 Galleria Dr A211, Middletown, NY 10941, USA

Website: Escape The Mystery Room

Opening hours: Mon - Sat: 10am - 9:30pm; Sun: 11am - 6pm

6. Bring your kids to Billy Beez

Editor's Note: There's no photo available at the time of writing

Are you looking for a heart-pumping activity to take your kids to engage in? Found at Galleria at Crystal Run on Galleria Drive, Billy Beez is the ultimate indoor play park where you can take your kids to play and fun. Kids will be able to bounce, run, jump, slide, and even climb. You can team up with your kids and just add to the excitement and fun. This is a perfect way to enjoy unforgettable family experiences as you create more bonds. From racing down the slides to climbing through the jungles, you will have a lot of things to do together as a family.

Billy Beez

Address: United States, New York, Middletown, N Galleria Dr, Galleria at Crystal Run, 1

Website: Billy Beez

Opening hours: Sun - Thu: 10am - 8pm; Fri & Sat: 10am - 9pm

7. Have fun at Urban Air Trampoline and Adventure Park

Jump House Trampoline Feet
Source: Pixabay

Photo is only for illustrative purposes

Urban Air Trampoline and Adventure Park is a children’s amusement center that is perfectly situated in Galleria at Crystal Run on Galleria Drive. This park offers the best opportunity for families to get together and do fun activities together. If you have your kid’s birthday party coming up, this is the perfect opportunity for you to do things differently and take it to the next level. There’s a whole heap of adventurous stuff here from trampolines, a warrior course, go-karts, virtual reality among many more. At Urban Air, this is where you will experience the ultimate adventure and enjoy some lasting memories.

Urban Air Trampoline and Adventure Park

Address: 1 Galleria Dr, Middletown, NY 10941, USA

Website: Urban Air Trampoline and Adventure Park

8. Enjoy a relaxing massage at Relax Zone & Spa

Spa Massage Relax
Source: Pixabay

Photo is only for illustrative purposes

This massage spa is found inside Galleria at Crystal Run in Middletown. Have you been working for the whole week and are exhausted? This is a nice place you can go and relax your body. They have a highly trained and experienced staff who will rub your back and leave you feeling totally relaxed. From foot massages to back massages, everything here is just on point. You can even go there for a manicure and pedicure and get your nails beautifully painted by the experts. If you have someone recovering from an injury or someone pregnant, this is a good place to take them for a massage

Relax Zone & Spa

Address: 1 Galleria Dr, Middletown, NY 10941, USA

Opening hours: Mon - Sat: 10am - 9:30pm; Sun: 11am - 6pm

9. Dine at Tony Boffa's

Pasta Italian Food Tasty
Source: Pixabay

Photo is only for illustrative purposes

Tony Boffa’s is a family-owned Italian restaurant that is perfectly situated on Railroad Avenue in Middletown and offering classic red-sauce fare in basic surroundings. Do you love Italian food? Tony Boffa’s is the next place where you should be dining if you are in Middletown. The restaurant serves fresh mouthwatering delights that are filling and addictive. Their menus are prepared from fresh locally acquired ingredients and expertly cooked by experienced chefs. The service you receive from the catering staff is top notch. You should make sure to stop by Tony Boffa’s and treat your taste buds to savory mouthwatering Italian delicacies.

Tony Boffa's

Address: 75 Railroad Ave, Middletown, NY 10940, USA

Website: Tony Boffa’s

Opening hours: Wed & Thu: 11am - 9pm; Fri & Sat: 11am - 10pm; Sun: 12pm - 9pm; (closed on Mon & Tue)

10. Visit the First Congregational Church

First Congregationalist Church of Middletown
Source: Photo by Wikimedia Commons user Daniel Case used under CC BY-SA 3.0

Are you a religious person visiting Middletown? The First Congregational Church is the place you should head to. Strategically located on Main Street, the church is one of the most visible landmarks of the city of Middletown. It’s unique and different from other churches in the area in that its spire stands taller than any structure within the vicinity. This historic church was established by a congregation of migrants who had come from New England. It was one of the first developments that attracted settlement in the area. You can attend a mass there or just visit for some spiritual inspiration.

First Congregational Church

Address: 35 E Main St, Middletown, NY 10940, USA

Website: First Congregational Church

11. Play 10-pin bowling at Round 1

Bowling Balls Sport
Source: Pixabay

Photo is only for illustrative purposes

Round 1 is an amusement center that is found in Galleria at Crystal Run. This is a place that operates multi-entertainment complexes that offer many different fun activities that you can participate in. You can go there with your spouse or friends and enjoy fantastic moments while engaging in activities such as bowling, billiards, ping pong, arcades, and karaoke. Finding its roots in Japan, now it has been embraced by the locals. You will find places to dine where you can treat your taste buds to some delicious delights. There’s also a bar where you can grab a drink as you relax and enjoy the entertainment.

Round 1

Address: 1 Galleria Dr Suite 01, Middletown, NY 10941, USA

Website: Round 1

Opening hours: 10am - 2am (daily)

12. Tour the Historical Society-Middletown

Editor's Note: There's no photo available at the time of writing

This is one of the major historical landmarks that attract people from all over the state and far. Historical Society-Middletown is a museum that is located on East Avenue that has a deep history of the historical people who lived in this city. Visit this museum and get to learn how this started as a glass manufacturing town and see the beautiful Tuthill Glass. This is where you will learn about the rich political and economic history of the historical residents and the heritage if Middletown. This museum is one of the treasures and heritage of Middletown and it is a major part of its history.

Historical Society-Middletown

Address: 25 East Ave, Middletown, NY 10940, USA

Website: Historical Society-Middletown

Opening hours: Thu - Tue: 1pm - 5pm (closed on Wed)

13. Play golf at Wallkill Golf Club

Golfer Golf Course
Source: Pixabay

Photo is only for illustrative purposes

Wallkill Golf Club is a beautiful golf course located in a tranquil and breathtaking surrounding. This Middletown, NY, attraction is in a lush cool environment with picturesque lagoons and beautiful trees overlooking the golf course. The lagoons provide such an intriguing challenge to play beside the water. If you are a fan of golf, then you wouldn’t want to miss the opportunity to watch or enjoy playing a golf match in such a romantic place. The flowery fairways are nicely manicured providing such a welcoming look. You can spend quality time with your loved one away from the activities of the city, playing golf in tranquility.

Wallkill Golf Club

Address: 40 Sands Rd, Middletown, NY 10941, USA

Website: Wallkill Golf Club

Opening hours: Mon - Fri: 6:30am - 8pm; Sat & Sun: 6am - 8pm

14. Enjoy a night out at Middletown Cabaret

Editor's Note: There's no photo available at the time of writing

Are you looking for a place to hang out or enjoy a fantastic nightlife? Middletown Cabaret is a nice place located in beautiful green scenery providing a romantic atmosphere. It is a unique place because it is only one of the few places that seems to embrace the 21st-century culture and is embracing the LGBTQ community without discrimination. The hospitality from the catering staff is top-notch. This place in Middletown, NY, also serves delicious and mouthwatering delicacies that you won’t find in any other bars. It’s a cool joint with a mellow mood and it’s very addictive. If you visit it once, you will definitely come back.

Middletown Cabaret

Address: 42 Ingrassia Rd, Middletown, NY 10940, USA

Website: Middletown Cabaret

Opening hours: Wed - Sun: 6pm - 4am (closed on Mon & Tue)

15. Indulge at DeStefano's Olde Erie

Editor's Note: There's no photo available at the time of writing

Are you tired after a long and busy week and you’re looking for a place to grab a drink to relieve your stress? If you don’t know what to do in Middletown, NY, DeStefano’s Olde Erie is the place you should be dropping by for a refreshing drink. This is a beautiful restaurant serving traditional Italian and American cuisines, including mouthwatering pasta, burgers, and succulent steak. This is the perfect place to take your loved one out for dinner and treat them to delicious, traditionally prepared culinary dishes. From the delicious chicken to the tasty steak, the menus here will make you salivate. You can enjoy a wonderful dinner with a complimenting glass of wine or a beer.

DeStefano's Olde Erie

Address: 7 W Main St, Middletown, NY 10940, USA

Website: DeStefano’s Olde Erie

Opening hours: Tue - Thu: 11:30am - 9pm; Fri: 11:30am - 10pm; Sat: 4pm - 10pm (closed on Sun & Mon)

Enjoy your time in Middletown, New York

Former O&W station, Middletown, NY
Source: Photo by user Daniel Case used under CC BY-SA 3.0

For whatever reason that brings you to Middletown, be it a vacation or business, you will be able to find a lot of fun and enjoy some beautiful moments during your stay here with this list of things to do that we have prepared for you.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Stephen Kinyanjui is an IT graduate who previously worked as an IT Assistant in a BPO company. He has an insatiable desire for traveling and adventure. He’s an artist who loves drawing and...Read more

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