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Drinks Events and Things to do in Chester, MD

Almost full
11/17- Annapolis, MD- Friendsgiving in Wine Country
Tue, Nov 17, 7:00 PM
Annapolis · Cooper’s Hawk Winery & Restaurant
Almost full
11/17- Annapolis, MD- Friendsgiving in Wine Country
Tue, Nov 17, 7:00 PM
Annapolis · Cooper’s Hawk Winery & Restaurant
2026 Bourbon Classic Charity Clay Shooting Tournament
Wed, Nov 18, 9:00 AM
Queenstown · The Point at Pintail
2026 Bourbon Classic Charity Clay Shooting Tournament
Wed, Nov 18, 9:00 AM
Queenstown · The Point at Pintail
Bead Bar at the Bar!- Jewelry Making Event at Dark Horse
Thu, Nov 19, 6:00 PM
Annapolis · Dark Horse
Bead Bar at the Bar!- Jewelry Making Event at Dark Horse
Thu, Nov 19, 6:00 PM
Annapolis · Dark Horse
Thanksgiving Brunch at Kent Island Resort
Thu, Nov 26, 10:00 AM + 1 more
Stevensville · Kent Island Resort
Thanksgiving Brunch at Kent Island Resort
Thu, Nov 26, 10:00 AM + 1 more
Stevensville · Kent Island Resort
Spaghetti Dinner Fundraiser 11/21/2026 5 - 8pm Kent Island Elks Lodge
Sat, Nov 21, 5:00 PM
Stevensville · Elks Lodge
Spaghetti Dinner Fundraiser 11/21/2026 5 - 8pm Kent Island Elks Lodge
Sat, Nov 21, 5:00 PM
Stevensville · Elks Lodge
Cookies & Cocktails
Fri, Nov 20, 6:30 PM
Stevensville · Kent Island Resort
Cookies & Cocktails
Fri, Nov 20, 6:30 PM
Stevensville · Kent Island Resort
Foodies + New Friends: Annapolis Dinner Club | Giving Back Edition
Tue, Nov 17, 7:00 PM + 2 more
Annapolis · Carpaccio Tuscan Kitchen & Wine Bar
Foodies + New Friends: Annapolis Dinner Club | Giving Back Edition
Tue, Nov 17, 7:00 PM + 2 more
Annapolis · Carpaccio Tuscan Kitchen & Wine Bar
Sales end soon
Bourbon & Cigar Experience: Smoke, Spirits & Autumn Sips:
Thursday at 6:00 PM
Stevensville · Kent Island Resort
Sales end soon
Bourbon & Cigar Experience: Smoke, Spirits & Autumn Sips:
Thursday at 6:00 PM
Stevensville · Kent Island Resort
Wine Knot
Wed, Nov 18, 6:30 PM
Annapolis · Annapolis School of Seamanship
Wine Knot
Wed, Nov 18, 6:30 PM
Annapolis · Annapolis School of Seamanship
Sales end soon
Foodies + New Friends: Annapolis Dinner + Coffee Club
Wednesday at 7:00 PM + 7 more
Annapolis · Restaurant of the Week
Sales end soon
Foodies + New Friends: Annapolis Dinner + Coffee Club
Wednesday at 7:00 PM + 7 more
Annapolis · Restaurant of the Week
Sales end soon
Elegant Afternoon Tea at Brampton 1860
Sun, Nov 15, 2:00 PM + 1 more
Chestertown · 25227 Chestertown Rd
Sales end soon
Elegant Afternoon Tea at Brampton 1860
Sun, Nov 15, 2:00 PM + 1 more
Chestertown · 25227 Chestertown Rd
6th Annapolis Santa Stroll from Peake Social!
Sat, Dec 5, 12:30 PM
Annapolis · Annapolis
6th Annapolis Santa Stroll from Peake Social!
Sat, Dec 5, 12:30 PM
Annapolis · Annapolis
Almost full
Laughs in the Lounge
Sat, Nov 14, 7:00 PM
Annapolis · Stan & Joe's Saloon
Almost full
Laughs in the Lounge
Sat, Nov 14, 7:00 PM
Annapolis · Stan & Joe's Saloon
Thanksgiving Take-Out
Wed, Nov 25, 12:00 PM
Saint Michaels · 209 S Talbot St
Thanksgiving Take-Out
Wed, Nov 25, 12:00 PM
Saint Michaels · 209 S Talbot St
Kinusaiga Workshop at Irish Pub Pasadena with Maryland Craft Parties
Wed, Dec 2, 6:00 PM
Pasadena · The Irish Pub Next Door
Kinusaiga Workshop at Irish Pub Pasadena with Maryland Craft Parties
Wed, Dec 2, 6:00 PM
Pasadena · The Irish Pub Next Door
Oysters and Wine: A Master Pairing Class
Thu, Dec 3, 6:30 PM
Stevensville · Kent Island Resort
Oysters and Wine: A Master Pairing Class
Thu, Dec 3, 6:30 PM
Stevensville · Kent Island Resort
The Resin Room - One Year Anniversary Celebration
Sat, Nov 14, 2:00 PM
Annapolis · The Resin Room
The Resin Room - One Year Anniversary Celebration
Sat, Nov 14, 2:00 PM
Annapolis · The Resin Room
Sales end soon
Music Bingo Night | Odenton MD | FREE Entry | Drink Specials | Every Tues
Tuesday at 7:00 PM + 9 more
Odenton · Buck Murphy's Bar & Grill
Sales end soon
Music Bingo Night | Odenton MD | FREE Entry | Drink Specials | Every Tues
Tuesday at 7:00 PM + 9 more
Odenton · Buck Murphy's Bar & Grill
2026 Twilight: Taste & Sip at Homestead Gardens
Fri, Nov 20, 6:00 PM
Davidsonville · Homestead Gardens
2026 Twilight: Taste & Sip at Homestead Gardens
Fri, Nov 20, 6:00 PM
Davidsonville · Homestead Gardens
Let's Do Trivia! at Ten Eyck Brewing, Queenstown, MD
Friday at 6:30 PM + 11 more
Queenstown · Ten Eyck Brewing Company
Let's Do Trivia! at Ten Eyck Brewing, Queenstown, MD
Friday at 6:30 PM + 11 more
Queenstown · Ten Eyck Brewing Company

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