What to do in Middletown, NY

Activities, attractions and tours

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What to do in Middletown

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Orange County Fairgrounds

8.0/5 (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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Day trip destinations from Middletown

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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.