7 Best Wineries near Middletown

Mazzaroth Vineyard Winery • $$
8333 Myersville Rd, Middletown

“This vineyard is amazing - we had such a great time visiting this afternoon. Garry is clearly very passionate and personable, and will take the time to discuss the winemaking process from growing the grapes, to blending and bottling. The wines are really delightful. We will definitely be back!“

5 Superb38 Reviews
Orchid Cellar Meadery and Winery Winery • $$
8546 Pete Wiles Rd, Middletown

“Very nice meads here. Good variety as well.“

4.7 Superb65 Reviews
Willow Oaks Craft Cider and Wine Winery •
6219 Harley Rd, Middletown

“Really phenomenal spot! Absolutely gorgeous, the ciders were very unique and tasty, the desert wine tasting was fantastic, family friendly small business. I’m excited to try the cheese board next time, we didn’t know food was available so we bought a picnic as did others. We bought so much fresh stuff including eggs and amazing figs, and are excited to cook the meat when we get home. Loved it, will be coming back again asap and with friends!“

4.4 Superb25 Reviews
Six Wicket Vineyards Wineries •
10819 Church Hill Rd, Myersville - 6 miles

“I have been on a wine hopping experience through Maryland with a friend, and I'm thrilled that Six Wicket called to us for a visit yesterday. The owner, Ed, was so generous and knowledgeable and caring about his 26000 plants, and he left that passion within me as we moved into the tasting room. Of course we had a quick play on the croquet court first! We both fell for the Cabernet Franc in Slovenian Oak, but every wine we tasted was lovely in its own way, a slightly unusual occurrence. :) So if you're thinking of a little wine adventure, don't miss this Vineyard! Everything about it was 'spot on' and delightful.“

5 Superb38 Reviews
Cool Ridge Vineyard Winery •
19638 Cool Hollow Rd, Hagerstown - 11.53 miles

“Visited today. What a great experience. Gary and Suzanne, husband/ wife who own and run the place, did the tasting. First, what a great couple. The tasting room is in their home and is the nicest place I've been. The wines were all very good to outstanding. We left with 8, the couple with us also 8, plus we had a bottle there. Every wine was well explained as to its making and what to expect. The attention to detail and personal service were exceptional.But you have to make appointment. Google is misleading. Not the owners' fault. It's their home and a small winery. But well worth calling ahead.“

5 Superb1 Reviews
Big Cork Vineyards Wineries • $$
4236 Main St, Rohrersville - 6.44 miles

“Beautiful winery in Northwest Maryland that was recommened to me by another winery in Leesburg VA. The property and drive there is so picturesque. They have a beautiful and modern looking tasting room. The wine was pretty solid with my favorite being the petite verdot. They have food onsite and the pizza was pretty good. Big Cork is strong Maryland winery and a great place to visit.“

4.4 Superb80 Reviews
Springfield Manor Winery Distillery Brewery Wineries • $$
11836 Auburn Rd, Thurmont - 9.81 miles

“We got married on October 10th 2024. From the moment we toured this venue the year prior we knew this would be it. The venue speaks for itself but my wife Raven and I really want to give thanks to Brian, Loree and the rest of the team at Springfield Manor. From the communications before the wedding to the wedding day itself they were fantastic.

Brian and the team were always responsive to our questions.
We also noticed how Brian treats his team members cuz it extended to how his team treated us and our guests .

We could tell that they serve with love and respect and it was evident how happy everyone was on our special day.“

4.3 Superb106 Reviews

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