Things to do in Middletown

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Photo by Vincent Ramundo
Photo by Vincent Ramundo

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What to do in Middletown

 

Looking for sports, concerts, or theater events in Middletown? Search event tickets to see what's happening today, or to plan what to do this weekend!

 

 

Discover the most popular places to visit in Middletown

Orange County Fair Speedway

4/5(5 reviews)

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

4.5/5(4 reviews)

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

4/5(20 reviews)

During your visit to Middletown, you can search for that perfect souvenir at Galleria at Crystal Run. While in this family-friendly area, you can savor the top-notch restaurants.

Galleria at Crystal Run

Paramount Theatre

3.5/5(28 reviews)

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

Though Orange Regional Medical Center might be what brings you to town, perhaps you'll have a chance to explore more of Middletown while you are here.

Orange Regional Medical Center

Touro College of Osteopathic Medicine

Though Touro College of Osteopathic Medicine might be what brings you to town, perhaps you'll have a chance to explore more of Middletown while you are here.

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 savor 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 savor 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 savor the top-notch restaurants.

Greenville Town Hall

 

Looking for fun things to do nearby? Check things to do near me to find and book the best things to do, fun activities, and top attractions wherever you happen to be.

 

 

Popular day trips from Middletown

Photo by Vincent Ramundo

Goshen

Photo by ViajandoconAna Rustrian

Montgomery

Port Jervis

Port Jervis

Photo by Eric Forbes

Pine Bush

Photo by Karen Wirtz

Slate Hill

Frequently asked questions

Is Middletown worth visiting?
Middletown has a unique mix of local charm, culture and attractions. Whether you're into outdoor activities, history or regional cuisine, there's a lot here to enjoy.
How do I spend a day in Middletown?
Harness Racing Museum and Hall of Fame and Orange County Arboretum are two good places to kick-start your sightseeing adventures. Be sure to check out the dining and retail options in Middletown while you're there too.
What is the top tourist attraction in Middletown?
You can't leave without visiting Paramount Theatre, rated the top tourist attraction in Middletown.
Is three days enough to stay in Middletown?
Three days in Middletown is more than enough to enjoy the city's key attractions. Many guests book for two days on average. Paramount Theatre, Harness Racing Museum and Hall of Fame and Highland Lakes State Park are among the top-rated sights. Want to see more? Stick around a little longer to check off nearby hotspots like Hudson River Valley.
Is Middletown a walkable city?
With popular neighborhoods and major sights within walking distance of the city center, Middletown is a good place to see on foot. Have fun wandering between Paramount Theatre and Orange County Fair Speedway. Then take a stroll through Mechanicstown, located 2 miles from the center, and Washington Heights, which is roughly 2 miles away.
What are some activities to do in Middletown with kids?
If you are after sights and tours for all the family, check out these awesome ideas for what to do in Middletown with kids.

What to do in Middletown for adults?
Whether you're a culture enthusiast, avid foodie or outdoor adventurer, there are lots of things to do in Middletown for adults.
Are there free things to do in Middletown?
One of the best ways to discover free things to do in Middletown is to ask a local tour guide. You'll get insider tips on cool neighborhoods, parks and other highlights you can visit without getting your cash out. Harness Racing Museum and Hall of Fame is one spot that doesn't charge an entrance fee.