Title: 10 TOP Things to Do in New Windsor October 2025 | Expedia.ca [Hotels in New Windsor](https://expedia.ca/New-Windsor-Hotels.d10021.Travel-Guide-Hotels)[New Windsor Car Rentals](https://expedia.ca/Car-Rentals-In-New-Windsor.d10021.Car-Rental-Guide)[New Windsor Vacation Packages](https://expedia.ca/New-Windsor.d10021.Destination-Travel-Guides) # What to do in New Windsor, NY ## Activities, attractions and tours ## Visit New Windsor Types of activities [New Windsor travel guide](https://expedia.ca/New-Windsor.dx10021) ![Photo by Wanderlustfemale](https://mediaim.expedia.com/destination/2/6747dae34f8ec5459e58210202f4caed.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Wanderlustfemale](https://mediaim.expedia.com/destination/2/6747dae34f8ec5459e58210202f4caed.jpg) ![Photo by Wanderlustfemale](https://mediaim.expedia.com/destination/2/069b19a0533a0b1edc4355725efa057d.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Wanderlustfemale](https://mediaim.expedia.com/destination/2/069b19a0533a0b1edc4355725efa057d.jpg) ![Photo by Wanderlustfemale](https://mediaim.expedia.com/destination/2/5fec30090ec6ee8d75204efc28c8eac4.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Wanderlustfemale](https://mediaim.expedia.com/destination/2/5fec30090ec6ee8d75204efc28c8eac4.jpg) ![Photo by gavvykins](https://mediaim.expedia.com/destination/2/c0c6e89f18c117192e2c5e6517452e90.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by gavvykins](https://mediaim.expedia.com/destination/2/c0c6e89f18c117192e2c5e6517452e90.jpg) ## New Windsor Attractions Let Expedia help you experience the best that New Windsor 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 New Windsor 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 New Windsor 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. #### New Windsor 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 New Windsor. 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 New Windsor 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 New Windsor | Number of things to do | 13 | | --- | --- | | Cheapest thing to do on Expedia | [Woodbury Common Premium Outlet Shopping Shuttle](https://expedia.ca/things-to-do/woodbury-common-premium-outlet-shopping-shuttle.a341934.activity-details): CA $59 | | Top 5 things to do | - [Woodbury Common Premium Outlet Shopping Shuttle](https://expedia.ca/things-to-do/woodbury-common-premium-outlet-shopping-shuttle.a341934.activity-details) - [Woodbury Common Premium Outlets Shopping Tour from Midtown](https://expedia.ca/things-to-do/woodbury-common-premium-outlets-shopping-tour-from-midtown.a46073505.activity-details) - [Woodbury Outlets Shopping 1-Day Tour from New York-Kids 50 Percent Off](https://expedia.ca/things-to-do/best-woodbury-outlets-shopping-1-day-tour-from-new-york.a44739311.activity-details) - [Shared Autumn Helicopter Tour from Westchester](https://expedia.ca/things-to-do/shared-autumn-helicopter-tour-from-westchester.a413464.activity-details) - [Cold Spring Town + Woodbury Outlets Shopping 1-day Tour](https://expedia.ca/things-to-do/cold-spring-town-woodbury-outlets-shopping-1-day-tour.a45259369.activity-details) | | Half-day tours | - [Beacon: Gourmet Beacon Food Tour](https://expedia.ca/things-to-do/beacon-gourmet-beacon-food-tour.a47933744.activity-details) - [Taste the Hudson Valley with Gourmet Beacon Food Tour](https://expedia.ca/things-to-do/taste-the-hudson-valley-with-gourmet-beacon-food-tour.a47114856.activity-details) | | With kids | - [Woodbury Common Premium Outlet Shopping Shuttle](https://expedia.ca/things-to-do/woodbury-common-premium-outlet-shopping-shuttle.a341934.activity-details) - [Woodbury Common Premium Outlets Shopping Tour from Midtown](https://expedia.ca/things-to-do/woodbury-common-premium-outlets-shopping-tour-from-midtown.a46073505.activity-details) - [Woodbury Outlets Shopping 1-Day Tour from New York-Kids 50 Percent Off](https://expedia.ca/things-to-do/best-woodbury-outlets-shopping-1-day-tour-from-new-york.a44739311.activity-details) - [Cold Spring Town + Woodbury Outlets Shopping 1-day Tour](https://expedia.ca/things-to-do/cold-spring-town-woodbury-outlets-shopping-1-day-tour.a45259369.activity-details) - [Taste the Hudson Valley with Gourmet Beacon Food Tour](https://expedia.ca/things-to-do/taste-the-hudson-valley-with-gourmet-beacon-food-tour.a47114856.activity-details) | ## What to do in New Windsor * * * ### Discover the most popular places to visit in New Windsor #### Kristi Babcock Memorial Park Kristi Babcock Memorial Park is just one of the places to see in New Windsor, so why not enjoy the other things to explore during your travels? You can attend a sporting event while in the area. [](https://expedia.ca/Kristi-Babcock-Memorial-Park-New-Windsor.d6182281.Vacation-Attraction) #### New Windsor Cantonment State Historic Site You can find out about the history of New Windsor with a stop at New Windsor Cantonment State Historic Site. You can attend a sporting event while in the area. [](https://expedia.ca/New-Windsor-Cantonment-State-Historic-Site-New-Windsor.d6171747.Vacation-Attraction) #### National Purple Heart Hall of Honor You can study the exhibits at National Purple Heart Hall of Honor, a museum with a storied past, during your trip to New Windsor. You can attend a sporting event while in the area. [](https://expedia.ca/National-Purple-Heart-Hall-Of-Honor-New-Windsor.d6182275.Vacation-Attraction) #### Knox's Headquarters State Historic Site You can spend an afternoon exploring the galleries in Knox's Headquarters State Historic Site during your travels in New Windsor. Check out the shops and top-notch restaurants in this family-friendly area. [](https://expedia.ca/Knoxs-Headquarters-State-Historic-Site-New-Windsor.d553248621532664460.Vacation-Attraction) #### Horizon Family Medical Group Though Horizon Family Medical Group might be what brings you to town, perhaps you'll have a chance to explore more of New Windsor while you are here. [](https://expedia.ca/Horizon-Family-Medical-Group-Newburgh.d624556188680130560.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 New Windsor ![Newburgh showing a marina and boating](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/59000/59968-Newburgh-And-Vicinity.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Newburgh [](https://expedia.ca/Newburgh.dx6023343) ![Photo by Trevor Romaine](https://mediaim.expedia.com/destination/2/e8aa509919fbeae0fc5affbfe8e57b92.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Cornwall-on-Hudson [](https://expedia.ca/Cornwall-On-Hudson.dx6338911) ![Photo by Wonderer](https://mediaim.expedia.com/destination/2/4debc0532114c2b653bbb414a56b9098.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Woodbury [](https://expedia.ca/Woodbury.dx553248634999102702) ## Frequently asked questions ### Is New Windsor worth visiting? > New Windsor offers a unique blend of culture, local charm and attractions. Whether you're into the outdoors, history or local culinary flavours, there's a lot here to enjoy. ### How do I spend a day in New Windsor? > Once you've checked off leading attractions like Motorcyclepedia Museum and Boscobel House and Gardens, spend some time enjoying New Windsor's shopping and dining scene. ### What is the top tourist attraction in New Windsor? > Dia Beacon is one of the top tourist attractions in New Windsor and deserves a spot on every to-do list of the area. ### Is three days enough to stay in New Windsor? > Three days will give you enough time to check out the leading city attractions, including Dia Beacon, Storm King State Park and Ritz Theatre. The average stay in New Windsor is two days. If you have the time to extend your getaway, Hudson River Valley isn't far away. ### Is New Windsor a walkable city? > Some major attractions in New Windsor, like Dia Beacon and Ritz Theatre, are within walking distance. You can also visit several of the city's popular neighbourhoods on foot. Only 3 kilometres from the city centre of New Windsor is Vails Gate and Firthcliffe is 5 kilometres away. ### What are some activities to do in New Windsor with kids? > If you're searching for tours and attractions for all of your group, we've got some awesome ideas for what to do in New Windsor with kids. > > > > - [Woodbury Common Premium Outlet Shopping Shuttle](https://expedia.ca/things-to-do/woodbury-common-premium-outlet-shopping-shuttle.a341934.activity-details) > - [Woodbury Common Premium Outlets Shopping Tour from Midtown](https://expedia.ca/things-to-do/woodbury-common-premium-outlets-shopping-tour-from-midtown.a46073505.activity-details) > - [Woodbury Outlets Shopping 1-Day Tour from New York-Kids 50 Percent Off](https://expedia.ca/things-to-do/best-woodbury-outlets-shopping-1-day-tour-from-new-york.a44739311.activity-details) > - [Cold Spring Town + Woodbury Outlets Shopping 1-day Tour](https://expedia.ca/things-to-do/cold-spring-town-woodbury-outlets-shopping-1-day-tour.a45259369.activity-details) > - [Taste the Hudson Valley with Gourmet Beacon Food Tour](https://expedia.ca/things-to-do/taste-the-hudson-valley-with-gourmet-beacon-food-tour.a47114856.activity-details) ### What to do in New Windsor for adults? > There are plenty of things to do in New Windsor, with activities for adults of all ages. Cap off your day with a visit to Benmarl Vineyards and Winery or Palaia Vineyards Winery. ### Are there free things to do in New Windsor? > From checking out parks to wandering around hip neighbourhoods, it's easy to discover free things to do in New Windsor. If you're stuck for ideas, ask for recommendations from a local tour guide. 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