Things to do in Middletown

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A large steel bridge spanning a river, surrounded by trees and buildings.
A steel arch bridge over a river with surrounding trees and buildings.
A calm lake at sunset with trees and grass along the shore.
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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!

 

 

Stay near popular Middletown attractions

A large Ferris wheel against a sunset sky.

Orange County Fairgrounds

8.0/10 (87 reviews)
This historic fairgrounds combines a century-old county fair with thrilling dirt track racing. Enjoy carnival rides during the July fair or catch heart-pounding motorsport action at the legendary speedway.
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Popular day trips from Middletown

An aerial view of a town with a river, industrial buildings, and a bridge.

Goshen

Two large silos, a barn, and a green field under a blue sky.

Montgomery

A rocky terrain with autumn foliage and distant views of a valley.

Port Jervis

A field of purple flowers with a green hillside in the background.

Wurtsboro

A snow-covered church with a steeple, surrounded by leafless trees and a snow-covered lawn.

New Hampton

A dense forest with tall trees and lush green ferns.

Pine Bush

A dog sitting on a bench by a calm lake surrounded by trees.

Slate Hill

A calm lake surrounded by trees with autumn foliage.

Otisville

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.

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