Title: 10 TOP Things to Do in Winchester November 2025 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d6056879.Travel-Guide-Hotels)[Flights to Winchester](https://expedia.ca/Cheap-Flights-To-Winchester.d6056879.Travel-Guide-Flights)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d6056879.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d6056879.Destination-Travel-Guides) # What to do in Winchester, VA ## Activities, attractions and tours ## Visit Winchester Types of activities Where to stay [Winchester travel guide](https://expedia.ca/Winchester.dx6056879) ![Winchester](https://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Photo by Kelly Godby](https://mediaim.expedia.com/destination/2/297d683bf6c02958194b1942fe08aec5.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Kelly Godby](https://mediaim.expedia.com/destination/2/297d683bf6c02958194b1942fe08aec5.jpg) ![Photo by Kelly Godby](https://mediaim.expedia.com/destination/2/f49e8a63a13c776ab427323a5e49834e.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Kelly Godby](https://mediaim.expedia.com/destination/2/f49e8a63a13c776ab427323a5e49834e.jpg) ![Photo by Kelly Godby](https://mediaim.expedia.com/destination/2/6d3b3982724040fc8a572ddcf2811938.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Kelly Godby](https://mediaim.expedia.com/destination/2/6d3b3982724040fc8a572ddcf2811938.jpg) ![Photo by Kelly Godby](https://mediaim.expedia.com/destination/2/06546ed83b202fba84d0142ab0abdc43.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Kelly Godby](https://mediaim.expedia.com/destination/2/06546ed83b202fba84d0142ab0abdc43.jpg) ## Winchester Attractions Let Expedia help you experience the best that Winchester 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 Winchester 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 Winchester 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. #### Winchester 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 Winchester. 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 Winchester 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 Winchester | Number of things to do | 1 | | --- | --- | | Cheapest thing to do on Expedia | [Shenandoah Tour: Self-Guided Drive](https://expedia.ca/things-to-do/shenandoah-national-park-self-guided-driving-tour.a5064646.activity-details): CA $24 | | Top 5 things to do | - [Shenandoah Tour: Self-Guided Drive](https://expedia.ca/things-to-do/shenandoah-national-park-self-guided-driving-tour.a5064646.activity-details) | | Half-day tours | | | With kids | | ## What to do in Winchester * * * ### Discover the most popular places to visit in Winchester ![Museum of the Shenandoah Valley](https://mediaim.expedia.com/destination/2/00bcc1929a21a52154c279eaecdf93f9.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Museum of the Shenandoah Valley 5/5(1 review) You can spend time exploring the galleries in Museum of the Shenandoah Valley during your trip to Winchester. Check out the top-notch restaurants or charming coffeehouses in this walkable area. [](https://expedia.ca/Museum-Of-The-Shenandoah-Valley-Winchester.d6127313.Vacation-Attraction) ![Handley Regional Library](https://mediaim.expedia.com/destination/2/73997bc29c1a471c7123089852c4944b.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Handley Regional Library 5/5(1 review) After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Check out the charming coffeehouses or top-notch restaurants in this walkable area. [](https://expedia.ca/Handley-Regional-Library-Old-Town-Winchester.d6164024.Vacation-Attraction) #### Winchester Medical Center Though Winchester Medical Center might be what brings you to town, perhaps you'll have a chance to explore more of Winchester while you are here. [](https://expedia.ca/Winchester-Medical-Center-Winchester.d6164057.Vacation-Attraction) #### Shenandoah University 4/5(1 review) Enjoy the collegiate vibe when you visit Shenandoah University, during your trip to Winchester. While in this walkable area, you can savor the top-notch restaurants. [](https://expedia.ca/Shenandoah-University-Winchester.d6127311.Vacation-Attraction) #### Apple Blossom Mall You can enjoy retail therapy at Apple Blossom Mall during your visit to Winchester. While in this walkable area, you can savor the top-notch restaurants. [](https://expedia.ca/Apple-Blossom-Mall-Winchester.d6164018.Vacation-Attraction) #### Shenandoah Valley Discovery Museum You can take time to visit Shenandoah Valley Discovery Museum during your travels to Winchester. While in this walkable area, you can savor the top-notch restaurants. [](https://expedia.ca/Shenandoah-Valley-Discovery-Museum-Old-Town-Winchester.d553248621587527659.Vacation-Attraction) #### Rock Harbor Golf Course Enjoy a round of golf in Winchester at Rock Harbor Golf Course. While in this walkable area, you can savor the top-notch restaurants. [](https://expedia.ca/Rock-Harbor-Golf-Course-Winchester.d553248621561864838.Vacation-Attraction) #### Bright Box Theater Enjoy a show at Bright Box Theater, a storied theater in Winchester. While in this walkable area, you can savor the top-notch restaurants. [](https://expedia.ca/Bright-Box-Theater-Old-Town-Winchester.d553248621561864843.Vacation-Attraction) #### Patsy Cline Historic House You can find out about the history of Winchester with a stop at Patsy Cline Historic House. While in this walkable area, you can savor the top-notch restaurants. [](https://expedia.ca/Patsy-Cline-Historic-House-Winchester.d553248621532661841.Vacation-Attraction) ### Explore areas of Winchester ![Default Image](https://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Old Town Winchester Old Town Winchester is known for its ample dining options, and you can make a stop by Bright Box Theater and Shenandoah Valley Discovery Museum while in the area. [](https://expedia.ca/Winchester-Old-Town-Winchester.dx6164092) ![Default Image](https://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Winchester Historic District While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Winchester Little Theater. [](https://expedia.ca/Winchester-Winchester-Historic-District.dx918789051029594112) * * * 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 Winchester ![Photo by Stephanie Sutton](https://mediaim.expedia.com/destination/2/0f9fdd213769c5b9ea606378c29239ea.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### White Post [](https://expedia.ca/White-Post.dx184119) ## Frequently asked questions ### Is Winchester worth visiting? > Winchester offers an interesting mix of culture, local charm and attractions. Whether you're into history, nature or traditional cuisine, there's a lot here to enjoy. ### How do I spend a day in Winchester? > After you've visited leading attractions like Shenandoah Valley Discovery Museum and Abram's Delight, spend some time discovering Winchester's retail and dining scene. ### What is the top tourist attraction in Winchester? > The top tourist attraction in Winchester is Shenandoah Valley Discovery Museum, so don't forget to put it on your sightseeing itinerary. ### Is three days enough to stay in Winchester? > You can easily tick off leading sights like Shenandoah Valley Discovery Museum, Winchester Little Theatre and Abram's Delight with a three-day getaway in Winchester. On average, many travellers book two days here. There's plenty to experience nearby too, so stay a bit longer and check out Loudoun County. ### Is Winchester a walkable city? > It all depends on what you'd like to see and do in Winchester. Several key attractions, such as Shenandoah Valley Discovery Museum and Winchester Little Theatre, are accessible on foot. If you're up for a stroll through some of Winchester's best neighbourhoods, Old Town Winchester is 0.16 kilometres away from downtown, while Winchester Historic District is 0.32 kilometres away from the city centre and also within walking distance. ### What are some activities to do in Winchester with kids? > If you are after attractions and activities for all the family, here are some terrific ideas for what to do in Winchester with kids. ### What to do in Winchester for adults? > There are lots of things to do in Winchester, with activities for adults of all ages. End the day with a visit to Valerie Hill Winery or Mt Hebron Cemetery. ### Are there free things to do in Winchester? > One of the simplest ways to find free things to do in Winchester is to speak with a local tour guide. You'll get insider recommendations on exciting neighbourhoods, parks and other hotspots you can experience without reaching into your pocket. Mt Hebron Cemetery is one place that doesn't charge an admission fee. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Other - [3 Star Hotels in Old Town Winchester](https://www.expedia.ca/3Star-Old-Town-Winchester-Winchester-Hotels.s30-n6164092-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Stephens City](https://www.expedia.ca/4Star-Stephens-City-Hotels.s40-0-d12076.Travel-Guide-Filter-Hotels) - [Hotels near Apple Blossom Mall](https://www.expedia.ca/Apple-Blossom-Mall-Hotels.0-l6164018-0.Travel-Guide-Filter-Hotels) - [Apartments in Boyce](https://www.expedia.ca/Boyce-Apartments.d184084-aaApartments.Travel-Guide-Accommodation) - [B&B in Boyce](https://www.expedia.ca/Boyce-Bed-And-Breakfast.d184084-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Boutique Hotels in Boyce](https://www.expedia.ca/Boyce-Hotels-Boutique-Hotel.0-0-d184084-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Boyce Hotels](https://www.expedia.ca/Boyce-Hotels.d184084.Travel-Guide-Hotels) - 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