Cookout Winchester, VA: Pleasant Valley Road Hours, Ratings and 11.8% Tax

Winchester taxes a Cook Out tray almost as hard as Charlottesville does. The City of Winchester charges a 6.5% meals tax on top of Virginia's 5.3% sales tax, 11.8% in all, which turns a $7.39 Regular Tray into $8.26. The restaurant at 1551 S. Pleasant Valley Road is rated 3.9 on Restaurantji and 4.2 on Google but 2.9 on Yelp, and reviewers say the lines are slow because there are not enough cashiers.

11.8%

Tax on a meal

6.5% city meals tax plus 5.3% sales tax

$8.26

Regular Tray with tax

Charlottesville, at 12.3%, is $8.30

4.2

Google rating

747 reviews via Wanderlog

2.9

Yelp rating

61 reviews, June 2026

Where does Winchester sit among Virginia's meal taxes?

Second to Charlottesville in our guides. Winchester's own tax page lists the 6.5% meals tax and the 5.3% sales tax, the latter as 4.3% state plus a 1% local rate. Council weighed a half-point increase in earlier budgets and the FY27 budget passed without raising it, so 6.5% is the current rate. The totals start from usual Cook Out prices, so the Pleasant Valley Road board may differ.

The Charlottesville guide and the Virginia guide cover the rest of the state.

What do Winchester diners say?

Reviewers praise the milkshakes and the value. A Restaurantji reviewer says service can be an issue because there are often not enough cashiers, which leads to long waits. Two Tripadvisor review titles read "Open up dining area !!" and "Improving but not much".