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Middletown

Middletown’s downtown has a movie palace at its center. Storefronts line the streets, and the Paramount Theatre’s marquee gives the walk through town a focal point.

Recommendations

Landmark4.5/5

Highland Lakes State Park

Embark on a nature-filled adventure at Highland Lakes State Park, where lush forests, serene lakes, and scenic hiking trails await. Bring your fishing gear or pack a picnic to enjoy by the water. With plenty of opportunities for outdoor fun, this park is a must-visit for nature enthusiasts and adventure seekers alike.

Landmark4.4/5

Orange County Fair Speedway

Get ready to rev your engines at Orange County Fair Speedway! Located in Middletown, NY, this iconic racetrack offers adrenaline-pumping action for all ages. Don't miss out on the fast-paced excitement and family-friendly atmosphere. Head over to 239 Wisner Ave and experience the thrill of racing in the heart of Orange County!

Shop4.2/5

Galleria at Crystal Run

Get ready to shop 'til you drop at Galleria at Crystal Run! This sprawling mall in Middletown, NY has everything you need for a fun day of retail therapy. With over 100 stores, restaurants, and entertainment options, you'll never run out of things to do. Don't forget to snap a selfie with the iconic crystal chandelier!

Eat$$$4.7/5

Piccolo Cucina e Vino

Looking for a taste of Italy in the heart of Middletown? Look no further than Piccolo Cucina e Vino! This cozy restaurant on North St serves up delicious pasta dishes, wood-fired pizzas, and an impressive wine selection. The intimate atmosphere and friendly staff make it a perfect spot for a romantic dinner or a relaxed evening with friends. Bellissimo!

Eat$$$4.5/5

DeStefano's Olde Erie

DeStefano's Olde Erie in Middletown offers a rich blend of Italian-American heritage and local history, featuring mouthwatering cuisine and a charming atmosphere that makes it a must-visit destination for food lovers.

Eat$$4.9/5

HolyDog

Eat$$4/5

Taco Bell

Taco Bell with a drive-through.

Stays

Stay4.05/5

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen in Middletown offers rooms with air-conditioning, private bathrooms, and free WiFi. Each room includes a work desk, sofa bed, and soundproofing for a restful stay. Guests can enjoy an indoor swimming pool, fitness centre, and hot tub. Additional amenities include a lounge, business area, and picnic area. The hotel provides a child-friendly buffet and free toiletries. Located 31 km from Stewart International Airport, the hotel is near attractions such as Morrison Hall (2.6 km) and National Shrine Of Our Lady Of Mount Carmel (2.8 km). Metro-North Harriman Station is 33 km away. Guests appreciate the room cleanliness, convenient location, and attentive property staff.

Stay4.05/5

Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown in Middletown offers spacious rooms with air-conditioning, free WiFi, and modern amenities. Guests enjoy amenities such as a fitness centre, indoor swimming pool, and a children's pool. The hotel features a fitness room, outdoor fireplace, and a games room. Additional facilities include a minimarket, grocery delivery, electric vehicle charging station, and barbecue areas. Free toiletries and a work desk enhance the stay. A complimentary American breakfast is served daily. The property offers a business area, outdoor seating, and family rooms, catering to all guest needs. Located 28 km from Stewart International Airport, the hotel is near attractions like Above The Clouds and Fantasy Balloon Flights, both 5 km away. Guests appreciate the room size and breakfast provided by the property.

Stay3.8/5

Hampton Inn Middletown

Hampton Inn Middletown in Middletown offers comfortable rooms with free WiFi, private check-in and check-out services, and family rooms. Guests enjoy amenities such as a fitness centre, saltwater swimming pool, and a lounge. A continental buffet breakfast is served daily, featuring warm dishes, fresh pastries, fruits, and juices. The hotel provides a business area, minimarket, and daily housekeeping service. Additional amenities include a fitness room, outdoor seating, and picnic area. Located 5 km from Above The Clouds and 6 km from Fantasy Balloon Flights, the hotel is also close to Morrison Hall and Soons Orchards. Stewart International Airport is 25 km away. Guests appreciate the room comfort, bed comfort, and attentive staff.

Stay4.6/5

Residence Inn by Marriott Middletown Goshen

Hotel in Middletown with a kitchen in every room, a pool and breakfast.

Stay4.4/5

Holiday Inn Express & Suites Middletown - Goshen by IHG

Looking for a cozy stay in Middletown, NY? Look no further than Holiday Inn Express & Suites! Enjoy complimentary breakfast, a fitness center, and free Wi-Fi. Just a short drive from the Galleria at Crystal Run and Orange County Fairgrounds. Book your stay at this IHG gem today!

Stay3.9/5

Courtyard by Marriott Middletown Goshen

Things To Do
Provided by

5/5

45 mins

45 Minute Scenic Horseback Trail Ride

Set against the backdrop of the breathtaking Hudson Valley (about an hour north of NYC), this 45-minute trail ride offers a unique opportunity to connect with nature on horseback. Accompanied by a skilled wrangler, riders will navigate through 117 acres of picturesque meadows, shaded woods, and a serene pond. No prior riding experience is necessary, as the skilled and friendly staff will ensure a safe and enjoyable ride. Keep an eye out for local wildlife as you traverse sunny fields. Suitable for ages 7 and up, this ride is perfect for families, friends, special events and celebrations, and beginners alike, promising a memorable adventure in the great outdoors with gentle horses. We also have a free petting zoo and offer pony rides for children 2 and up.

$105.00

5/5

4 h

Helicopter Engagement Experience from NYC to Glenmere Mansion

Create an unforgettable proposal with a private helicopter journey from Manhattan to the elegant Glenmere Mansion. Begin with a scenic NYC tour, taking in landmarks like the Statue of Liberty and Central Park before flying over the Hudson Valley. Land directly at the estate, where a butler will escort you to a reserved table for a refined three-course, farm-to-table lunch, complete with a champagne toast. Stroll through the manicured gardens to find the perfect secluded proposal spot, surrounded by picturesque lakeside views. Capture the moment with a professional photographer, preserving memories to last a lifetime. Enhance the experience with an optional 60-minute couples massage at the Glenmere Spa, adding relaxation to your celebration. Conclude your day with a private helicopter flight back to Manhattan, enjoying one last skyline view. Availability: year-round. Flight time: ~30 minutes each way. Total duration: ~4 hours. Subject to mansion and photographer availability.

$12,100.00

5/5

Walkway Over the Hudson & Wineries- Private Transport

The Walkway Over the Hudson is the longest and highest elevated pedestrian bridge in the world! Benmarl Winery is America's oldest Vineyard! When you accompany two of those facts with a company that will bring you to and from your locations with professionalism, reliability and friendliness, you can't go wrong! Don't feel guilty indulging one bit at your wineries because you got some exercise in during your amazing time at the Walkway Over the Hudson! Optional bike rentals are available upon request for the Walkway Over the Hudson. Please let us know ahead of time. *Hotel accommodations are available upon request. Simply send us an email and we will be happy to assist you. *Depending on winery availability at the time of your booking, it may be necessary to visit different comparable local wineries than listed. *the Walkway Over the Hudson is a flat paved walkway that is 1.30 miles long. You will get picked up on the other side.

$235.00

4.2/5

2 h

2-Hour Small Group Central Park Bike Tour

Embark on a 2-hour journey around one of the world's most beautiful parks — a guided, 2-hour, small-group, Central Park bike tour. Explore its hidden secrets and enjoy the sites of Central Park — with personal service from a local, licensed tour guide. See the historic architecture, movie sites, gardens, hidden waterfalls, and much more. Along the way, learn about New York City's most-popular green space.

$119.00

4.1/5

LEGOLAND® New York Theme Park Admission Ticket

Discover endless family fun at LEGOLAND® New York Resort — the ultimate LEGO® theme park destination for kids ages 2–12! Located in the heart of the Hudson Valley, this unforgettable theme park invites families to ride, climb, splash, and build across seven immersive LEGO themed lands. Experience world exclusive attractions like the LEGO® Factory Adventure Ride, where you’ll transform into a Minifigure. Test your ninja skills on LEGO® NINJAGO® The Ride, embark on a medieval quest aboard the Dragon Coaster, and explore stunning miniature cities built entirely from LEGO bricks in MINILAND. Plus, don’t miss the all new LEGO Ferrari Build & Race experience, where kids can design, build, test, and race their own LEGO Ferrari on digital and physical tracks. From thrilling rides to hands on building adventures, awesome awaits at LEGOLAND New York! Brick or Treat runs every day the park is open this October!

$49.99

Hudson Valley Wineries- Private Transport- OR brewery/distillery

Benmarl Winery is America's oldest Vineyard! When you accompany that fact with a company that will bring you to and from your locations with professionalism, reliability and friendliness, you can't go wrong! We can't wait to book your reservations, make your itinerary, provide you with transportation (by us or one of our partnered transportation companies). You'll love all 3 of your winery stops for the day! Visit our website for more detailed information. Hotel accommodations are available upon request. Send us an email and we'll be happy to book you in a hotel or a private vacation rental (VRBO or Airbnb). Depending on availability, it may be necessary to visit different comparable local wineries than listed. Whichever winery we choose will also be enjoyable of course! We have lots of wineries in our area. We also can conduct your winery tour in other areas than what's listed such as Dutchess County, Ulster County, Columbia County and or Orange County. Email us for questions.