St. Michaels Happening Happy Hours
- nancy9487
- Oct 11
- 3 min read
Best Happy Hour Deals in Walkable Downtown St. Michaels
I love visiting St. Michaels, Maryland! It's one of the most charming small towns I've ever explored. Talbot Street, the main downtown street, is lined with delicious restaurants, adorable gift shops, clothing boutiques and art galleries. I always find the most unique gifts when I shop there.
After a deep dive online and a weekend visit to St. Michaels, these are the scheduled weekly happy hours I discovered. Other restaurants seem to also offer special cocktail and food deals, just not on a regular recurring schedule.
I've ranked these spots according to the best happy hour pricing for both cocktails and food. All of these fun restaurants/bars are conveniently located near each other, making them easily walkable, except for the Inn at Perry Cabin. It's slightly farther, about 1/2 mile from the town center. (I always love to walk, so this wasn't a deterrent for me.)
See the map below to chart out your happy hour walking tour.
St. Michaels Happy Hour Specials
Address: 305 S Talbot St
Happy Hour: Thurs & Sat 3pm - 6pm
Cocktail Specials:
$3 Domestic Beers
$4 Import Beers
$5 Rail Drinks
$6 House Glass Wine
$6 Crushes
Food Specials:
50% Off Appetizers
Why Go: Beautiful Historic Building, Several Outdoor & Indoor Dining Areas
Address: 403 S Talbot St
Happy Hour: Mon, Thurs, Fri 4:30pm - 6pm (bar area only)
Cocktail Specials:
$3 Domestic Beer
$4 Hard Cider & ESB Amber
$5 Import & Domestic Craft Beer
$7 Glass Wine
$8 Rail Cocktails & Martinis
$9 Bistro Cosmo & Italian Manhattan
Food Specials:
$12 - $17 Fancy Nibbles
Why Go: Charming Inviting Atmosphere, Variety of Seating Options, Upscale Cuisine
Address: 209 N Talbot St
Happy Hour: Mon - Fri 4pm - 6pm
Cocktail Specials:
$4 Domestic Beer
$8 Glass Wine
$10 Manhattan, Mid-Day Martini
$11 HH Buck
Food Specials:
$2 - $9 Appetizers Including Oysters, Salad, Fries & Burger
Why Go: Creative Cocktails & Extensive Wine List, Oyster Bar
Address: 209 S Talbot St
Happy Hour: Mon - Fri 2pm - 6pm
Cocktail Specials:
$2 Off Draft Beers
$7 Crushes Any Flavor
$1 Off House Glass Wines
Food Specials:
$10 Appetizers Wings, Flatbreads, Cream of Crab Soup, Quesadillas, Queso Dip
Why Go: Great Casual Tavern Atmosphere, Delicious Food
Address: 125 Mulberry St
Late Night Happy Hour: Everyday 8PM - Close
Cocktail Specials:
$2 Natie Light Beer Cans
$5 Fireball & Lemon Drops
$6 House Margarita
Food Specials:
$8 - $15 Appetizers Including Mozzerella Sticks, Edemame, Wings, Cesear Salad
Why Go: Waterfront Fun Island Vibe, Extensive Cocktail Menu
Address: 310 S Talbot St
Happy Hour: Fri 4pm - 6pm, Sun 12pm - 4pm
Cocktail Specials:
Fri All Cocktails Discounted - Details Not Listed
$6 Select Draft Beers (Sun)
$8 Crushes (Sun)
$7 Mimosas (Sun)
Food Specials: None Listed
Why Go: Self-Serve Wine & Taproom, Interactive Fun Experience
Address: 409 S Talbot St
Happy Hour: Mon - Fri 4pm - 6pm
Cocktail Specials:
$5 Off Glass Wine, Featured Cocktails, Domestic Bottles
Food Specials:
None Listed
Why Go: Outdoor Patio with Retractable Roof & Fireplaces, Extensive Beer & Wine List
Address: 407 S Talbot St
Happy Hour: Tues - Sun 4pm - 6pm
Cocktail Specials:
Specially Priced Domestic Beers, Featured Cocktails & Glasses of Wine
Food Specials:
Happy Hour Bites
Half Plate Happy Hour - Smaller Portions of Chef Selected Dishes
Why Go: Casual New Orleans Vibe Offering Refined Menu, Named "Best Steakhouse" in Eastern Shore 2025
Address: 200 S Talbot St
Happy Hour: Mon - Fri 3:30pm - 7pm
Cocktail Specials:
$1 Off All Drinks
Mon & Tues 1/2 Price Bottles of Wine (Excludes Super Tuscans)
Food Specials: None Listed
Why Go: Authentic Italian Cuisine, Lively Mediterranean Vibe with Pass-Through Bar to Patio
Address: 308 Watkins Ave
Happy Hour: Fri Sept/Oct 3pm - 6pm
Cocktail Specials:
Crisp Cocktails Offered (No Mention of Pricing)
Food Specials:
Special Small Bites Menu
Why Go: Live Music Series Waterfront - Back Patio Area
St. Michaels is a fantastic destination year-round! I hope you enjoy sipping a cocktail at any of these places mentioned.
For additional fun outings in Maryland, check out my posts on a fun bar crawl and a perfect day out in Annapolis!
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