Wineries & Breweries in Chestertown
The most complete and owner-verified listings first — hours, phone, website, services. No pay-to-play.
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Lands Point Winery and Vineyards
22620 Handy Point Rd, Chestertown, MD 21620-4017
Fri-Sat 12pm-7pm
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Bad Alfred's Distilling
323 High St, Chestertown, MD 21620
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Riley's Mill Ale Works
860 High St, Chestertown, MD 21620
Of the 3 wineries & breweries listed in Chestertown, 2 give a phone number, 1 publishes opening hours and 3 have a website. The nearest bigger selection is Dundalk with 4.
More locations within 30 miles of Chestertown
Only 3 locations listed in Chestertown itself, so here are the closest ones in nearby towns. Distance is straight-line from Chestertown.
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Owl Have Another Brewery
4.9 mi · 12058 Parson Hill Ct, Worton, MD 21678-1333
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Willow Wineries
6.7 mi · 7020 Rock Hall Rd, Rock Hall, MD 21661
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Cassinelli Winery And Vineyards
9.5 mi · 3830 Church Hill, MD 21623, Church Hill, MD 21623
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Rock Hall Brewing Co
9.7 mi · 5781 N Main St, Rock Hall, MD 21661
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Patriot Acres Farm Brewery
12.8 mi · 1621 Millington Rd, Sudlersville, MD 21668
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Tilmon's Island Winery
13.3 mi · 755 Millington Rd, Sudlersville, MD 21668
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Bull & Goat Brewery
13.4 mi · 204 Banjo Ln, Centreville, MD 21617
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Old Courthouse Distilling
13.4 mi · 204 Banjo Ln Ste E, Centreville, MD 21617
Guides for location shoppers
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OwningThe Ultimate Guide to Charcuterie Boards: Styling, Pairings, and Recipes
Learn how to build balanced charcuterie and cheese boards, from festive holiday trees and brunch platters to portable grazing cups and effortless wine pairings.
OwningCrystal Wine Glassware Guide: Types, Brands, Care, and Stemless Styles
A practical guide to selecting, maintaining, and understanding crystal wine glassware, covering traditional stems, modern tumblers, sparkling vessels, and mineral compositions.
BuyingUnderstanding Bold Reds: Dry Wines, Tannin Profiles, and Old Vine Zinfandels
This guide breaks down what makes red wine dry, how tannins shape mouthfeel, what defines a full-bodied Cabernet, and why old vine Zinfandel earns its distinct reputation.
Maryland statewide, by feature
- Breweries and Beer Gardens in Maryland220
- Wineries and Vineyards in Maryland147
- Bottle Shops in Maryland96
- Wineries with Food in Maryland74
- Wine Bars in Maryland64
- Wineries with Tastings in Maryland63
- Distilleries in Maryland56
- Wineries with Outdoor Seating in Maryland41
- Winery Tours in Maryland23
- Dog-Friendly Wineries in Maryland21
- Wineries Offering Wine by the Glass in Maryland5