Best Happy Hours in Downtown Annapolis
- nancy9487
- Oct 3
- 4 min read
Bars & Restaurants Walking Distance from Annapolis City Dock
I've combined two of my favorite things, a great happy hour deal and taking a walk! Here's 10 of the best Annapolis happy hour deals, all within a mile of Annapolis City Dock. With this, you can park your car and explore these great restaurants and bars on foot.
See the map below to chart out your happy hour walking tour.
My Favorite Annapolis Happy Hour Deal
Hands down, this is the best happy hour deal in downtown Annapolis! If you're up for a walk, take the trek over the Spa Creek Bridge into Eastport. Note: plan on arriving early for this happy hour to secure a seat. The Chart House offers their happy hour specials only if you're seated at the bar or one of their bar tables - and these spots fill up fast!
Address: 300 Second Street, Annapolis (1 mile from Annapolis City Dock)
Happy Hour: Mon - Fri 4:30pm - 6:30pm
Cocktail Specials:
$5 - $5.75 Beers
$6 Well Spirits
$8 Premium Spirits
$9 Cocktails
$10 Premium Glass Wines
Food Specials:
$7 - $13 Appetizers including lettuce wraps, fish tacos and prime rib sliders. Check out their menu for all of the tasty deals.
Why Go: Beautiful Waterfront View, Elegant Upscale Atmosphere, Amazing Deals on Food & Drinks
The Chart House is one of the few places offering great happy hour prices on premium drinks and cocktails. And the food is delicious - definitely substantial enough to qualify as dinner!
Best Downtown Annapolis Happy Hour Specials
Address: 400 Sixth Street, Annapolis (.6 miles from Annapolis City Dock)
Happy Hour: Mon - Fri 3pm - 6pm (bar only), Rooftop Thurs 6pm - 9pm
Cocktail Specials:
$5 Bottle Beer
$7 Draft Beer
$5 Well Drinks
$5 Glass Wine
$9 Specialty Cocktails
Food Specials:
Half Price Select Appetizers, Flatbreads & Wings
Why Go: Live Music on Fridays 4pm - 7pm and Rooftop Thursdays 6pm - 9pm
Address: 400 Fourth Street, Annapolis (.8 miles from Annapolis City Dock)
Happy Hour: Mon - Thurs 3pm - 6pm (excluding holidays)
Cocktail Specials:
$5 Canned & Draft Beers
$5 Well Drinks
$5 Glass Wine
$10 - $13 Cocktails
Food Specials:
$1 Oysters
$5 - $10 Appetizers
Why Go: Fun Nautical Vibe, Locals Favorite
Address: 110 Compromise Street, Annapolis (.1 miles from Annapolis City Dock)
Happy Hour: Mon - Fri 3pm - 6pm (at bar)
Cocktail Specials:
$4 Beer
$7 Glass Wine
$8 House Spirits
Food Specials:
$9 - $10 Appetizers, Sandwiches & Oysters
Why Go: Best Waterfront Location in the Heart of Annapolis - Ego Alley
Address: 193B Main Street, Annapolis (.3 miles from Annapolis City Dock)
Happy Hour: Mon - Fri 3pm - 6pm
Cocktail Specials:
$3 Bottled Beer
$5 Draft Beer
$5 Well Drinks
$5 Glass Wine
$5 Punch
Food Specials:
$3 - $5 Appetizers, $15 Sample This Platter
Why Go: Cool Speakeasy Vibe Located on Main Street
Address: 63 Maryland Avenue, Annapolis (.3 miles from Annapolis City Dock)
Happy Hour: Mon - Fri 3:30pm - 6:30pm
Cocktail Specials:
$3.50 - $4.50 Bottled & Draft Beers
$5 Glass Wine
$4 Well Drinks
$5 - $7.50 Cocktails
Food Specials:
$4 - $9 Appetizers
Why Go: One of my favorite spots! Amazing Irish Pub Atmosphere, Delicious Food
Address: 2 Market Space, Annapolis (less than .1 miles from Annapolis City Dock)
Happy Hour: Mon - Fri 3pm - 7pm
Cocktail Specials:
$4 - $5 Draft Beers
$5 Glass Wine
$9 Specialty Cocktails
$2 Oyster Shooters
Food Specials:
All Appetizers 1/3 off regular price
$9 Crab Ball Slider
Why Go: Annapolis Must See - Established in 1790
Reynolds Tavern & 1747 Pub
Address: 7 Church Circle, Annapolis (.4 miles from Annapolis City Dock)
Happy Hour: Sun - Thurs 4pm - 6pm
Cocktail Specials:
$5 Draft Lager
$6 Glass Wine
$6 Pub Punch
Food Specials:
$5 - $10 Appetizers
Why Go: Charming Beer Garden, Lots of History
Address: 33 West Street, Annapolis (.5 miles from Annapolis City Dock)
Happy Hour: Mon - Fri 3pm - 6pm
Cocktail Specials:
$3.50 Domestic Bottle Beer
$5 Draft Beer
$2 Off Wine & Liquor
Food Specials:
1/2 Off Appetizers
Why Go: Large Historic Restaurant, English-Style Pub, Wisteria Covered Brick Patio
Address: 37 West Street, Annapolis (.5 miles from Annapolis City Dock)
Happy Hour: Mon - Fri 4pm - 7pm
Cocktail Specials:
All Beer - Half Price
All Liquor - Half Price (excluding top shelf)
All Cocktails - Half Price (some restrictions)
Food Specials: none listed
Why Go: Local Fun Dive bar, Outside Patio, Lots of Entertainment
There's no better place to enjoy a cocktail than the picturesque setting of downtown Annapolis! I hope you enjoy exploring some of the places I've highlighted.
For additional fantastic Annapolis outings, check out my posts on a fun bar crawl and a perfect day out!
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