This historic town blends a countryside charm with a bustling downtown.
Spend an afternoon exploring everything from an independent book store to a modern day apothecary to antique shops.
There’s also kayaking on the lower Shenandoah River in the warmer months.
Credit:Heather Bien
And, luckily, Frederick County, where Winchester is located, is known for its fruitful farm stands.
Get the brisket and eggs for a taste of both.
They brew Lone Oak Coffee, which is a local roaster located just minutes from the shop.
Credit:Heather Bien
Try the Smithfield Luau for the perfect combination of a Hawaiian pizza and classic Virginia ham.
You’ll find microbreweries, cideries, and breweries that also serve food and welcome dogs.
Grab a seat on the rooftop for a pre-dinner drink if you have to wait for a table.
Credit:Heather Bien
wyndhamhotels.com, 103 E Piccadilly St, Winchester, VA 22601
Credit:Heather Bien
