A beautiful city located in the Shenandoah Valley of Virginia, Winchester is home to a centuries-old historic district with buildings dating back 250 years, charming shops, delicious restaurants, and numerous historical landmarks and museums waiting to be explored.
Take a leisurely stroll through its tree-lined streets or stop by one of the museums on your way back from a day out exploring the surrounding area.
If you’re up for something a little more active, head to Jim Barnett Park with its many scenic trails, BMX track, and year-round public pool.
You can also go for a walk or a bike ride in the Abrams Creek Wetlands on the outskirts of town. When it comes time to relax, step inside one of the many local pubs or grab lunch at one of the neighboring eateries.
Does this sound like the kind of place you’d like to visit? If so, continue reading for a comprehensive list of all the area has to offer
The 28 Most Popular Things To Do In Winchester, Virginia
28. 18th Century Valley Cabin
5.0 (1 review)
Location: Winchester VA
Web Address: https://winchesterhistory.org/18th-century-valley-cabin/
27. Winchester-Frederick County Historical Society
5.0 (4 reviews)
Credit: Brent Moore, License, Flickr
Location: 1340 S Pleasant Valley Road Winchester VA
Tel: 540 662 6550
Web Address: https://winchesterhistory.org/
26. Wilkins Lake
4.5 (8 reviews)
25. Abrams Creek Wetlands Preserve
4.9 (10 reviews)
Credit: Chesapeake Bay Program, License, Flickr
Location: W Jubal Early Dr Winchester VA
Tel: 540 662 4946
Web Address: https://winchesterva.gov/parks/abrams-creek-wetlands-preserve
24. Newtown History Center
4.6 (13 reviews)
Credit: Waud, Alfred R., License, Wikimedia commons
Location: 5408 Main Street Streetephens City VA
Tel: 540 869 1700
Web Address: http://newtownhistorycenter.org/
23. Fort Collier Civil War Center
4.1 (19 reviews)
Credit: jim catalfamo, Google Maps
Location: 922 Martinsburg Pike Winchester VA
22. Fort Loudoun Historic Site
3.9 (22 reviews)
Credit: Jerrye Roy Klotz,, License, Wikimedia commons
Location: 419 N Loudoun Street Winchester VA
Tel: 703 574 6110
Web Address: http://frenchandindianwarfoundation.org/about-us/fort-loudoun/
21. The trails at the MSV
4.7 (24 reviews)
Credit: Pamela Hart, Google Maps
Location: 901 Amherst Street Winchester VA
20. Lake Holiday
4.8 (29 reviews)
Credit: velodenz, License, Flickr
19. Shawnee Springs Preserve
4.3 (61 reviews)
Credit: Shawnee Springs Preserve, Google Maps
Location: 512 Hollingsworth Dr Winchester VA
Tel: 540 662 4946
Web Address: https://su.edu/su-bries/su-bries-home/natural-places/shawnee-springs-preserve/
18. Kernstown Battlefield
4.7 (114 reviews)
Credit: AgnosticPreachersKid, License, Wikimedia commons
Location: 610 Battle Park Dr Winchester VA
Tel: 540 450 7835
Web Address: http://kernstownbattle.org/
17. Rose Hill Park
4.7 (118 reviews)
Location: 1871 Jones Road Winchester VA
Web Address: https://themsv.org/visit/rose-hill
16. Haunted Nightmares
4.6 (120 reviews)
Credit: Haunted Nightmares, Google Maps
Location: 933 Barley Ln Winchester VA
Tel: 540 667 7377
Web Address: http://hauntednightmares.net/
15. James Charles Winery & Vineyard
4.3 (144 reviews)
Credit: James Charles Winery & Vineyard, Google Maps
Location: 4063 Middle Road Winchester VA
Tel: 540 931 4386
Web Address: http://jamescharleswine.com/
14. Third Winchester Battlefield Park
4.6 (209 reviews)
Location: 541 Redbud Road Winchester VA
Tel: 540 740 4545
Web Address: https://shenandoahatwar.org/third-winchester-battlefield-park
13. Sherando Park
4.6 (366 reviews)
Credit: Zachary Tasler, Google Maps
Location: 255 Lakeview Cir Streetephens City VA
Tel: 540 665 5678
Web Address: http://fcva.us/departments/parks-recreation/parks/sherando-park
12. Marker-Miller Orchards
4.7 (564 reviews)
Credit: Sarah Stierch, License, Wikimedia commons
Location: 3035 Cedar Creek Grade Winchester VA
Tel: 540 662 1391
Web Address: http://markermillerorchards.com/
11. Clearbrook Park
4.7 (941 reviews)
Location: Community Dr Clear Brook VA
Tel: 540 665 5678
Web Address: http://co.frederick.va.us/
10. Jim Barnett Park
4.6 (1,397 reviews)
Credit: Jim Barnett Park, Google Maps
Location: 1001 E Cork Street Winchester VA
Tel: 540 662 4946
Web Address: http://winchesterva.gov/parks/
Our Top picks
9. Abram’s Delight
4.5 (39 reviews)
Credit: APK, License, Wikimedia commons
Location: 1340 S Pleasant Valley Road Winchester VA
Tel: 540 662 6519
Web Address: https://winchesterhistory.org/abrams-delight/
8. Winchester-Frederick County Visitor Center
4.7 (95 reviews)
Location: 1400 S Pleasant Valley Road Winchester VA
Tel: 540 542 1326
Web Address: http://visitwinchesterva.com/
7. George Washington’s Office
4.5 (109 reviews)
Credit: Sarah Stierch, License, Wikimedia commons
Location: 32 W Cork Street Winchester VA
Tel: 540 662 4412
Web Address: https://winchesterhistory.org/george-washingtons-office/
6. Shenandoah Valley Civil War Museum
4.6 (130 reviews)
Credit: Antony-22, License, Wikimedia commons
Location: 20 N Loudoun Street Winchester VA
Tel: 540 542 1145
Web Address: http://shenandoahatwar.org/civil-war-museum
5. Stonewall Jackson’s Headquarters
4.8 (220 reviews)
Credit: APK, License, Wikimedia commons
Location: 415 N Braddock Street Winchester VA
Tel: 540 667 5505
Web Address: https://winchesterhistory.org/stonewall-jacksons-headquarters/
4. Patsy Cline Historic House
4.6 (227 reviews)
Credit: Sarah Stierch, License, Wikimedia commons
Location: 608 S Kent Street Winchester VA
Tel: 540 662 5555
3. Shenandoah Valley Discovery Museum
4.7 (641 reviews)
Location: 19 W Cork Street Winchester VA
Tel: 540 722 2020
Web Address: http://discoverymuseum.net/
2. Museum of the Shenandoah Valley
4.7 (911 reviews)
Location: 901 Amherst Street Winchester VA
Tel: 888 556 5799
Web Address: http://themsv.org/
1. Old Town Winchester
4.6 (1,277 reviews)
Credit: Jerrye Roy Klotz,, License, Wikimedia commons
Location: 136 S Loudoun Street Winchester VA
Tel: 540 542 1326
Web Address: http://oldtownwinchesterva.com/
Final Words:
Thank you for reading our list of the best things to do in Winchester, Virginia! We hope it helped you plan the perfect itinerary for your next trip to this fantastic destination. Happy travels!
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