Things to do in Middletown

Activities, attractions and tours

Photo by Vincent Ramundo
Photo by Vincent Ramundo

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What to do in Middletown

Popular places to visit

Orange County Fair Speedway

Catch an event at Orange County Fair Speedway during your trip to Mechanicstown. Discover the area's festivals and churches.

Orange County Fair Speedway

Orange County Fairgrounds

Enjoy an outing to Orange County Fairgrounds during your stay in Mechanicstown. Discover the area's festivals and churches.

Orange County Fairgrounds

Galleria at Crystal Run

During your visit to Middletown, you can do some window-shopping at Galleria at Crystal Run. While in this family-friendly area, you can savour the top-notch restaurants.

Galleria at Crystal Run

Paramount Theatre

You can enjoy a show at Paramount Theatre on your trip to Middletown. While in this family-friendly area, find time to visit its shops.

Paramount Theatre

Orange Regional Medical Center

If Orange Regional Medical Center is what brings you to town, hopefully you'll have a chance to explore more of Middletown.

Orange Regional Medical Center

Touro College of Osteopathic Medicine

If Touro College of Osteopathic Medicine is what brings you to town, hopefully you'll have a chance to explore more of Middletown.

Touro College of Osteopathic Medicine

Highland Lakes State Park

You can take time to visit Highland Lakes State Park during your travels to Middletown. While in this family-friendly area, you can savour the top-notch restaurants.

Highland Lakes State Park

Highland Lake

Commune with nature and explore the great outdoors at Highland Lake during your travels in Middletown. While in this family-friendly area, you can savour the top-notch restaurants.

Highland Lake

Greenville Town Hall

Greenville Town Hall is just one of the places to see in Middletown, so why not enjoy the other things to explore during your travels? While in this family-friendly area, you can savour the top-notch restaurants.

Greenville Town Hall
Photo by ViajandoconAna Rustrian

Montgomery

Port Jervis

Port Jervis

Frequently asked questions

Is Middletown worth visiting?
Middletown has a unique mix of culture, local charm and attractions. Whether you're into nature, history or local culinary flavours, there are many things to enjoy here.
How do I spend a day in Middletown?
Harness Racing Museum and Hall of Fame and Orange County Arboretum are two awesome places to begin your adventures. Be sure to check out the dining and shopping options in Middletown while you're here too.
What is the top tourist attraction in Middletown?
You can't leave without checking out Paramount Theatre, ranked the top tourist attraction in Middletown.
Is three days enough to stay in Middletown?
Three days in Middletown is more than enough to visit the city's main highlights. Many guests book for two days on average. Paramount Theatre, Highland Lakes State Park and Harness Racing Museum and Hall of Fame are among the most popular sights. Want to see more? Stick around a while longer to visit nearby hotspots such as Hudson River Valley.
Is Middletown a walkable city?
It all comes down to what you want to do and see in Middletown. Several top sights, including Paramount Theatre and Orange County Fair Speedway, are reachable on foot. If you're up for a stroll through some of Middletown's best neighbourhoods, Mechanicstown is 3 kilometres away from downtown, while Washington Heights is 3 kilometres away from the centre and also within walking distance.
What are some activities to do in Middletown with kids?
Planning what to do in Middletown with kids has never been easier. Whether you're travelling with teenagers or toddlers, there are loads of family-friendly attractions to keep them entertained here.

What to do in Middletown for adults?
From tasty dishes and cultural gems to outdoor adventures and one-of-a-kind experiences, there are many fun things to do in Middletown for adults.
Are there free things to do in Middletown?
From enjoying parks to strolling around vibrant neighbourhoods, it's simple to find free things to do in Middletown. If you need new ideas, ask a local tour guide for recommendations. Highland Lakes State Park is a must for anyone looking to save on their sightseeing activities.