Okay, let me begin by saying this area has a serious addiction to ice cream. And let me be clear that this isn’t a criticism in any way. In fact, pair this with the affinity for great coffee (see our local coffee shops post), and you’re pretty much set when you visit over the summer.
Now, I’ve occasionally had to make some tough sacrifices for this job, and one of them is the many ice cream cones I’ve had to eat in order to accurately write this blog. You’re welcome. Somebody had to do it.
Seriously, though, I sincerely hope you have a chance to check out at least one or two of the below listed shops the next time you’re in the Winchester area (by the way, don’t hesitate to let us know if I missed anything!).
This is one of the only spots in the region that serves up custard and Italian ice. Located in a former Rita’s Italian Ice building, the owners decided to keep on offering the very popular frozen custard, Italian ice, and “gelati” which is a layered version of these two frozen treats. Don’t worry, you can still get your outstanding coffee, breakfast sandwiches and grilled cheeses here, too. Best of all, they’re open year-round so you don’t have to wait until spring to get your custard fix! 2430 Valley Ave, Winchester, VA 22601
Our southernmost sweet tooth haven, this small family-owned ice cream shop offers up soft serve, scoop ice cream and a full ice cream menu, with many delicious desserts to choose from. Located just down the street from Lord Fairfax Community College, they’ve got that coveted outside patio seating to fully enjoy our beautiful, laid back warm summer evenings. 7597 Main St, Middletown, VA 22645
Craig and Diana (the C and D of this establishment) have carved out a very busy little spot here on Rt 50 just a minute or two west of Valley Health Hospital. The best of both worlds, you can have your caffeine and sugar fix at the same time here. Featuring single origin volcanic soil coffee and locally made Garber’s ice cream, this is a must stop when exploring our beautiful countryside! 2953 Northwestern Turnpike, Winchester, VA 22602
A few years after 5 year old Mattie, a kindergartner at a local elementary school, died unexpectedly in 2005, her aunt and uncle sought out and opened up an ice cream truck to keep her memory alive. Today, the distinctive 33-foot long purple bus can be seen around town, often parked near the Martin’s supermarket on Rt. 7 near I-81. They have creative, rotating flavors but you’ll always find Mattie’s favorite, the banana split with a cherry on top, on their menu. Check out their Facebook page for their current schedule! Location varies – check Facebook page for schedule
Save up your appetite before you attempt one of these insane milkshakes! If you’re escaping the summer heat inside the Apple Blossom Mall, this spot is well worth the visit. In addition to single, mega and “New York style” sizes of milkshake, they have traditional scoop ice cream available in cones and bowls. This location, just opened in early 2021, is their second; the first being in Harrisonburg. 1850 Apple Blossom Dr, Suite 169, Winchester, VA 22601.
Opened in early 2014, this husband and wife operation took the place of the former McCoy’s Dairy Bar. This completely new ownership has made high quality, fun foods their focus. In addition to regionally sourced ice cream, they have an array of quick summer foods like hot dogs, funnnel cakes and fries. And be careful, they’ll deep fry just about anything. Their Easter special? Deep fried Cadbury eggs. Their summer best seller? Deep fried Oreo cookies… 320 Fairfax Pike, Stephens City, VA 22655
Owners Kathy and Brian Lewis opened Middleburg Creamery in 1996, and relocated to the Old Town Winchester pedestrian mall in late 2010. This is a true creamery that makes everything from scratch. Kathy is the ice cream guru, whipping up many great classic and seasonal flavors. Far from just a creamery, though, they have a scratch kitchen that turns out local favorites like chicken salad, rotisserie chicken, chili, soups, baked goods and more. 146 N Loudoun St, Winchester, VA 22601
Pack’s Frozen Custard / Dairy Corner (4 locations)
Pack’s is a local institution – a regional chain started several decades ago by the one and only Mrs. Pack – where you’ll get a very similar but not identical experience at each of our four local remaining locations. When Mrs. Pack retired a few years ago, we understand that the locations were bought by either close family or long-time employees. Now, a word to the wise, if you’ve never had true custard before, take it easy Chief. This is some seriously rich awesomeness in a cone. And go prepared for a line, especially on Friday and Saturday evenings all summer.
Disclaimer – no businesses paid us or gave us anything to be on this list – we just love sweet treats and our local businesses, as we hope you do when you visit!