Middletown (New York) Travel Guide

Discover the best attractions, activities, food, and accommodations in Middletown, New York. Our guide provides everything you need to know to plan your trip.


Introduction to Middletown (New York)

Middletown (New York) is a charming city located in Orange County, nestled in the heart of the Catskills Mountains. It is a perfect retreat for those looking for a relaxing getaway from the hustle and bustle of the city. Middletown offers visitors a wide range of attractions, from cultural sites to natural wonders, outdoor adventures, and excellent cuisine.

List of Places to Visit in Middletown (New York)

If you’re wondering what to see in Middletown, we have you covered. Here’s a list of places to visit in the city that you shouldn’t miss:

Culturally Important Attractions: Museums and Historical Places

Middletown is home to several museums, including the Historical Society of Middletown and Wallkill Precinct, which showcases the city’s rich history. The Museum at Bethel Woods, located on the site of the famous 1969 Woodstock Festival, features exhibits about the iconic music festival and its impact on culture.

For history enthusiasts, visit the Minisink Valley Historical Society, which houses collections of artifacts related to the region’s history. And, don’t miss the Orange County Veterans Memorial Cemetery, where you can pay your respects to the brave men and women who have served in the military.

Natural Attractions of Middletown (New York): Outdoor Adventures and Scenic Views

The great outdoors is one of Middletown’s main attractions. The city is surrounded by stunning natural beauty, including hiking trails, waterfalls, and scenic views. Take a leisurely stroll to one of the city’s beautiful parks, such as Fancher-Davidge Park or Maple Hill Park, or venture to nearby Bear Mountain State Park for more challenging hiking trails.

For those who love to fish, O&W Rail Trail offers excellent fishing opportunities. Those who prefer water activities should rent a kayak or go canoeing down the Wallkill River.

Hiking/Biking Routes of Middletown (New York)

The Catskills Mountains surrounding Middletown provide endless opportunities for hiking and biking. Here are some of the best trails to explore in the area:

  • High Point State Park
  • Minnewaska State Park Preserve
  • Mohonk Preserve

Best Things to Do in Middletown (New York): Activities and Tours

Besides exploring the hiking trails and natural beauty of Middletown, there are plenty of other things to do in the city. Here are some top-rated activities to try during your stay:

  • Visit the local vineyards and wineries such as Brotherhood Winery or Warwick Valley Winery and Distillery
  • Attend a show or concert at the Orange County Fair Speedway or the Paramount Theatre
  • Take a pottery class at the Create Community Arts Center
  • Go shopping in the city’s quaint downtown area

Week-Long Itinerary for Middletown (New York)

Middletown provides the perfect place for a week-long vacation. Here’s how to explore the city in a week:

  • Day 1: Visit the Museum at Bethel Woods and the Orange County Veterans Memorial Cemetery
  • Day 2: Explore Bear Mountain State Park and hike up to the Perkins Memorial Tower
  • Day 3: Rent a kayak or go canoeing on the Wallkill River, followed by a visit to Fancher-Davidge Park
  • Day 4: Drive to nearby Minnewaska State Park Preserve and enjoy the magnificent views of the Hudson River Valley
  • Day 5: Visit local vineyards and wineries such as Brotherhood Winery and Warwick Valley Winery and Distillery
  • Day 6: Take a pottery class at the Create Community Arts Center, followed by some shopping in the city’s downtown area.
  • Day 7: Head to High Point State Park for a day hike and picnic before returning back to Middletown

Food and Drink Scene of Middletown (New York)

Middletown offers a diverse culinary scene, with great options for foodies to indulge in. Here are some must-try dishes and local beverages:

Must-Try Dishes

  • The Reuben sandwich at Delancey’s Restaurant
  • The Philly Cheesesteak at Mia’s Kitchen
  • The chicken riggies at Cosimo’s Brick Oven

Local Beverages

  • The Angry Orchard Hard Cider, made locally in Walden, NY
  • Brotherhood Winery’s award-winning wines
  • Heritage Distilling Company’s craft spirits

Where to Stay in Middletown (New York): Hotels, Hostels, and Guesthouses

Middletown has a variety of accommodations that cater to travelers on any budget and preferences. Here are some of the best options:

  • Hilton Garden Inn Middletown
  • Quality Inn & Suites Middletown
  • Home2 Suites by Hilton Middletown

What to Buy in Middletown (New York)

Middletown offers a variety of souvenirs and local products to bring home. Some of the best items to purchase include:

  • Handmade pottery and crafts from the Create Community Art Center
  • Local beer, wine, and spirits from the vineyards and distilleries
  • Fresh produce from the local farmers’ market

Local Culture and Customs of Middletown (New York)

Middletown is steeped in a diverse culture and history. Take a minute to research customs and courtesies, and be mindful of the different traditions and values held by the local community.

Best Time to Visit Middletown (New York)

The best time to visit Middletown is during the fall months when the weather is mild and pleasant, and the foliage turns beautiful shades of red, yellow, and orange. The spring and summer months are also a great time to visit the city to take advantage of outdoor activities and events.

Do’s and Don’ts of Middletown (New York)

Do:

  • Respect local customs and cultures
  • Take advantage of outdoor activities and scenic views

Don’t:

  • Litter
  • Trespass on private properties

Safety and Health

Safety in Middletown (New York)

Middletown is a relatively safe city, with crime rates comparable to other small cities across the country. As a precaution, always be mindful of your surroundings and avoid walking alone late at night.

Health in Middletown (New York)

Middletown has a reliable healthcare system, with several hospitals and clinics available in the area. Travelers should make sure that they have the right insurance to cover any medical emergencies during their stay.

Getting to Middletown (New York): Transportation Options and Logistics

Middletown is easily accessible by car or public transportation. Here are some transportation options to consider:

Airports Near Middletown (New York)

  • Stewart International Airport (SWF)
  • Newark Liberty International Airport (EWR)
  • John F. Kennedy International Airport (JFK)

Bus Stations Near Middletown (New York)

  • ShortLine Bus
  • Coach USA

Other Options

  • Take the train via MTA Metro-North Railroad to get to Middletown

How to Get Around in Middletown (New York)

It’s easy to get around Middletown on foot, by bike, or by car. Rental cars and taxis are also available. Consider taking local cab companies such as Orange County Taxi or Johnson Transportation Inc.

Where to Go Next from Middletown (New York): Nearby Destinations and Excursions

Middletown serves as an excellent base to explore nearby destinations in the Hudson River Valley, such as New Paltz, Kingston, and Woodstock.

Conclusion

Middletown is a charming city that is full of natural beauty, history, and adventure. This comprehensive guide provides you with all the information you need to plan your trip and experience the best of what this city has to offer. Whether you’re traveling solo or with family or friends, Middletown is sure to provide an unforgettable experience.

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