Things to do in Winchester
171 places, local favorites first.
Sort: Local favorites · A to Z
Peppertree VA Apartments
Landmark and historical building · 221 Peppertree Ln
The Lofts at Jubal Square
Landmark and historical building · 1864 Old Jube Sq
FASST Sports Performance Training
Fitness trainer · 1117 Berryville Ave
AMC CLASSIC Apple Blossom 12
Drive in theater · 1850 Apple Blossom Dr
Meadow Branch Apartments
Landmark and historical building · 424 Ridgewood Ln
Orchardcrest Apartments
Landmark and historical building · 2524 Wilson Blvd
Shenandoah Conservatory Arts Academy
Theaters and performance venues · 203 S Cameron St
Shenandoah Valley Discovery Museum
Childrens museum · 19 W Cork St
Winchester-Frederick County Historical Society
Museum · 1340 S Pleasant Valley Rd
Shenandoah University - Bowman Building
Campus building · 2 S Cameron St
USTMA - United States Taekwondo Martial Arts Academy
Martial arts club · 2243 Papermill Rd
On the map
Where these 171 places are in Winchester.
Talk & tips
Favorites, openings and closings from Winchester neighbors.
Weigh in
Is Bro Bears Drive Thru Coffee the best coffee in Winchester?
Your answer becomes a post in Town Square.
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Some place details from Overture Maps (CDLA-Permissive-2.0), checked against the Census town line. Places added by neighbors go live once a second neighbor confirms them. Spot a mistake? Open the place and tap Edit mode.
How we sort and count
Each list puts neighbor favorites first (ratings and photos), then the most complete listings (a website, a phone number, a note), with local, independent spots ahead of national chains. Categories come from each place’s map category, so a café filed under “Shops” still shows up with the cafés. “A five-minute walk” is a quarter mile from the busiest spot on the map. Per-1,000 figures use the Census population.