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Middletown

Middletown, NY , USA

Middletown

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Middletown

Welcome to Middletown, NY! Known for its charming downtown area, historic architecture, and vibrant arts scene, this quaint town offers a perfect blend of small-town charm and city amenities. From exploring local boutiques to dining at delicious cafes, Middletown has something for every traveler to enjoy. Don't forget to check out the annual festivals and events that bring the community together!

Recommendations

Outdoor4.5/5

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 on Dolson Ave in Middletown, NY is a colorful oasis for hungry travelers. This Mexican-inspired fast food joint is perfect for a quick and tasty bite on the go. So grab some nachos or a burrito, and fuel up for your next adventure!

Stays

Stay4.55/5

Residence Inn by Marriott Middletown Goshen

Experience the charm of Residence Inn Middletown Goshen, where cozy suites meet modern amenities, perfect for extended stays and unforgettable memories in the heart of New York's picturesque Hudson Valley.

Stay4.5/5

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!

Stay4.05/5

Home2 Suites by Hilton Middletown

Discover Home2 Suites by Hilton Middletown, where modern comfort meets convenience, offering spacious suites, complimentary breakfast, and a welcoming atmosphere perfect for both business and leisure travelers exploring the scenic Hudson Valley.

Stay4.05/5

Sleep Inn & Suites Middletown - Goshen

Stay3.8/5

Hampton Inn Middletown

Welcome to Hampton Inn Middletown! Conveniently located near shopping and dining at Crystal Run Crossing. Relax in our comfortable rooms, take a dip in the indoor pool, and enjoy a complimentary hot breakfast. With friendly staff and modern amenities, your stay will be a breeze. Happy travels!

Stay3.65/5

Courtyard Middletown Goshen

Things To Do
Provided byViator

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.

$95.00
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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
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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
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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
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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! Experience the ultimate celebration of play during LEGO® Festival from July 20th to August 31!

$49.99
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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.

$235.00
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45 mins

Date Night a 45 minutes Trail Ride

Your Date Night Experience Ride immerses you in the Hudson Valley’s natural beauty. Saddle up for a guided horseback trek through wooded trails, open fields, and blooming meadows, then pause for photo ops with your horse. After the ride, gather around a cozy fire pit on the lawn, where a curated charcuterie board, s’mores kit, and a choice of wine or sparkling cider await. Late‑afternoon rides reward you with a spectacular sunset over the barn. Ideal for couples, families, or groups celebrating birthdays, anniversaries, engagements, parties, Mother’s or Father’s Day, a memorable night out now!!

$160.00
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