Title: 10 TOP Things to Do in Middletown October 2025 | Expedia.ca [Hotels in Middletown](https://expedia.ca/Middletown-Hotels.d8864.Travel-Guide-Hotels)[Flights to Middletown](https://expedia.ca/Cheap-Flights-To-Middletown.d8864.Travel-Guide-Flights)[Middletown Car Rentals](https://expedia.ca/Car-Rentals-In-Middletown.d8864.Car-Rental-Guide)[Middletown Vacation Packages](https://expedia.ca/Middletown.d8864.Destination-Travel-Guides) # What to do in Middletown, NY ## Activities, attractions and tours ## Visit Middletown Types of activities [Middletown travel guide](https://expedia.ca/Middletown.dx8864) ![Photo by Vincent Ramundo](https://mediaim.expedia.com/destination/2/b3592d5854c5ebf058517b7fb1df474d.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Vincent Ramundo](https://mediaim.expedia.com/destination/2/b3592d5854c5ebf058517b7fb1df474d.jpg) ## Middletown Attractions Let Expedia help you experience the best that Middletown has to offer! If you’re looking for fun itinerary ideas, we can provide you with a list of the top sightseeing attractions, as well as helping you to find unmissable activities. Whether you’re travelling with your family, planning a romantic trip with your loved one, or visiting on business, we’ll make it easy to plan an unforgettable holiday that checks all the boxes. #### Activities and Tours Middletown is crammed with must-see places to visit and things to do. We can help you decide where to stay, and make it a breeze to explore the surrounding areas with our guides on where to go, what to see and when to see it. No matter how long your stay, it’s easy to find places of interest in Middletown to make sure that you enjoy your experience to the fullest and don’t miss a thing. Leave the local knowledge to us and leave the hassle behind. If you’re planning a visit, why not check out our handy guides to places of interest in the area? You can browse lists of things to do, learn about the most popular attractions, and get help with planning the details of your trip. Expedia makes it easy for you to check out all the top sights. #### Middletown Attractions Expedia has something for everyone, so whether you’re planning to get active on a summer holiday, put a spring in your step with a romantic rendezvous, or pamper yourself with a leisurely winter trip, you’ll find plenty of attractions to keep you entertained. In addition to scheduling local tours, booking reservations and scoring advance event tickets, Expedia makes it easy to book your flight, hotel and rental car in advance, all on one consolidated travel itinerary, making for hassle-free travel and freeing you up to explore the sights of Middletown. Looking for things to do can be time consuming, but we can take the hassle out of planning your holiday. Whether you’re looking to get active in the great outdoors, sample the cuisine or catch up with the vibrant local culture, our guides to Middletown attractions ensure that you’ll have a successful trip, whatever the season. * * * ![find price illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__find_price.svg) ### Explore activities Explore thousands of experiences from activities and attractions to day tours and transfer. ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Book with ease Skip the line- book tickets online in minutes to top attractions with free cancellation on many activities. ![trophy illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Treat yourself Members save % or more when you book activities. * * * ## Recommended things to do in Middletown | Number of things to do | 2 | | --- | --- | | Cheapest thing to do on Expedia | [LEGOLAND New York Resort Admission Ticket](https://expedia.ca/things-to-do/legoland-new-york-resort-admission-ticket.a4125131.activity-details): CA $70 | | Top 5 things to do | - [LEGOLAND New York Resort Admission Ticket](https://expedia.ca/things-to-do/legoland-new-york-resort-admission-ticket.a4125131.activity-details) - [Private Van: Orange County Airport (SNA) to Los Angeles Cruise Terminal](https://expedia.ca/things-to-do/private-van-orange-county-airport-sna-to-los-angeles-cruise-terminal.a49210364.activity-details) | | Half-day tours | | | With kids | - [LEGOLAND New York Resort Admission Ticket](https://expedia.ca/things-to-do/legoland-new-york-resort-admission-ticket.a4125131.activity-details) | ## What to do in Middletown * * * ### Discover the most popular places to visit in Middletown #### Orange County Fair Speedway Catch an event at Orange County Fair Speedway during your trip to Mechanicstown. Discover the area's festivals and churches. [](https://expedia.ca/Orange-County-Fair-Speedway-Middletown.d6182288.Vacation-Attraction) #### Orange County Fairgrounds Enjoy an outing to Orange County Fairgrounds during your stay in Mechanicstown. Discover the area's festivals and churches. [](https://expedia.ca/Orange-County-Fairgrounds-Middletown.d6225664.Vacation-Attraction) #### Galleria at Crystal Run 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. [](https://expedia.ca/Galleria-At-Crystal-Run-Middletown.d6225666.Vacation-Attraction) #### 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. [](https://expedia.ca/Paramount-Theatre-Middletown.d553248621561106035.Vacation-Attraction) #### 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. [](https://expedia.ca/Orange-Regional-Medical-Center-Newburgh.d624549502712524800.Vacation-Attraction) #### 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. [](https://expedia.ca/Touro-College-Of-Osteopathic-Medicine-Middletown.d909916158766071808.Vacation-Attraction) #### 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. [](https://expedia.ca/Highland-Lakes-State-Park-Newburgh.d637211988758130688.Vacation-Attraction) #### 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. [](https://expedia.ca/Highland-Lake-Middletown.d876921236230545408.Vacation-Attraction) #### 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. [](https://expedia.ca/Greenville-Town-Hall-Middletown.d907927942378655744.Vacation-Attraction) * * * Looking for fun things to do nearby? Check [things to do near me](https://www.expedia.ca/things-to-do-near-me) to find and book the best things to do, fun activities, and top attractions wherever you happen to be. * * * ## Day trip destinations from Middletown ![Port Jervis](https://mediaim.expedia.com/destination/1/08c81db48e4587b7b1ffb2103a1900a0.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Port Jervis [](https://expedia.ca/Port-Jervis.dx9382) ![Photo by Eric Forbes](https://mediaim.expedia.com/destination/2/c75ccae0b1097e2389b5425bb9d38177.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Pine Bush [](https://expedia.ca/Pine-Bush.dx183706) ![Photo by Karen Wirtz](https://mediaim.expedia.com/destination/2/026dd56cf523ba8c831de057da7b2fda.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Slate Hill [](https://expedia.ca/Slate-Hill.dx6325187) ## 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. > > > > - [LEGOLAND New York Resort Admission Ticket](https://expedia.ca/things-to-do/legoland-new-york-resort-admission-ticket.a4125131.activity-details) ### 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. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - [Bullville Hotels](https://www.expedia.ca/Bullville-Hotels.d3000350713.Travel-Guide-Hotels) - [Beach Hotel Hotels in Orange County](https://www.expedia.ca/Destinations-In-Orange-County-Beach-Hotel.0-0-d553248635083901431-tBeachHotel.Hotel-Filter-Destinations) - [Cheap Hotels in Orange County](https://www.expedia.ca/Destinations-In-Orange-County-Cheap-Hotels.0-0-d553248635083901431-tCheapHotels.Hotel-Filter-Destinations) - [Hotels with a Pool in Orange County](https://www.expedia.ca/Destinations-In-Orange-County-Hotel-With-Pool.0-0-d553248635083901431-tHotelwithPool.Hotel-Filter-Destinations) - [Luxury Hotels in Orange County](https://www.expedia.ca/Destinations-In-Orange-County-Luxury-Hotel.0-0-d553248635083901431-tLuxuryHotel.Hotel-Filter-Destinations) - [Pet-Friendly Hotels in Orange County](https://www.expedia.ca/Destinations-In-Orange-County-Pet-Friendly-Hotel.0-0-d553248635083901431-tPetfriendlyHotel.Hotel-Filter-Destinations) - 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