> At Home Around the Chesapeake Bay: Happy Hours

Happy Hours

Some of these suggestions may change since my last update. If you find a great happy hour place or that one of my suggested places has changed, be sure to email me with an update! 


I am often asked for suggestions to dining locations for tasty morsels without breaking the piggy bank so I put together this list (and it is always growing or changing) of places that you can check out for their Happy Hours. Why Happy Hour?

Certainly, there is no shortage of incredible places to eat throughout Maryland. However, many of these restaurants can be a bit on the pricey side for those seeking a nice meal and maybe a spirited beverage to accompany the meal. With the average glass of wine in the area ranging from $10-$15 per glass, you might find your meal over $50pp. *Ouch!*

That's where these happy hour opportunities provide the opportunity to eat out once in a while without resorting to eating Ramen noodles the other days of the week. Not only do these suggestions provide exceptional value with really tasty eating for those on a budget, many of the selections provided are real meals and healthy eating options, not the typical "bar" food.

While this list may be limited right now to the Greater Annapolis vicinity, I am always expanding and adding to the list so look for areas outside of my hometown and be sure to check back frequently!

(For my fellow vegans/vegetarians, I have noted whether a happy hour has some vegan/vegetarian options.)

Jalapeno's Tapas Bar & Restaurant (Vegan/Vegetarian Selections available)
Spanish/Basque & Mexican gourmet
85 Forest Plaza
Annapolis Maryland 21401
Phone: (410) 266-7580

Happy Hour ~ 7 Days a Week in Bar area only
  • 4pm to 7pm, Monday - Thursday
  • 4pm to 6pm Friday & Saturday
Happy Hour food and drink:
  • Over 40 tapas and appetizers between $6-$7 each
  • Beers, $3
  • White Sangria, $5
  • Red Sangria, $5
  • Margarita, $5
The location of this restaurant wouldn't make you think that it is the gem that it is until you enter the restaurant. Gonzalo is one of the owners and he is the most charming and welcoming European gentleman you would want to greet you. The full service, sit-down waitstaff restaurant is designed with tile flooring, wall murals, a central fire place and elegant tile topped dining tables with European flair. The restaurant area is intimate and quiet enough for business or romantic dining. The full restaurant menu is on the higher priced side. The food is usually excellent. You will find live flamingo dance performances on selected days posted on their window as well as live music on other dates. 

The bar area is where you'll find the amazing (and affordable) Happy Hour menu. It is small bar area with a few tables, high tops and a bar counter with television. Locals know this happy hour place and it fills up fast.

Brio's Tuscan Grill of Annapolis (Limited Vegan/Vegetarian Selections, Gluten Free may be available)
Parole Towne Center
305 Sail Place
Annapolis, MD 21401
(410) 571-5660

Happy Hour ~ 5 Days a Week, Bar/outdoor lounge area
  • 3:30pm - 6:30pm Monday-Friday
  • 9:00pm - 11pm Monday - Friday Late night Happy Hour
  • Wednesdays feature $5 Martinis
  • Thursdays feature $5 Wine Pours
This is a chain restaurant offering full wait staffed seated restaurant dining as well as a separate bar area and outdoor bar/lounge seating. The bar/lounge area is large enough to accommodate larger parties and happy hour is only available in the bar/lounge area.

The Happy Hour food menu offers selections between $4 to $6 for small plate-sized items such as margherita or sausage/pepperoni flatbreads, tomato buffalo mozzarella salad, white bean & artichoke dip, Brio burger with fries or black pepper shrimp over crispy eggplant. (see website link above for current menu & events.)

Rams Head Tavern  (Very Limited Vegan/Vegetarian Selections)
Craft Beer Brewery, Restaurant & Bar
Historic City of Annapolis
33 West Street
Annapolis, MD 21401
(410) 268-4545

Happy Hour ~ 5 Days a Week, Bar area/outdoor rear garden area
Late Night Food Available ~ 7 Days a week until midnight, appetizers
  • 4pm - 7pm, Monday - Friday: $3 draft beers, $2 off all wine and liquor
  • 5pm - 7pm, Monday: Meatballs in a tangy sauce, free
  • 5pm - 7pm, Tuesday: Seafood Mania! Mussells, Oysters & Shrimp, free
  • 4pm - 7pm, Tuesday: 1/2 Price Wine Night
  • 5pm - 7pm, Wednesday: Carved meat selections of ham, beef and turkey, free
  • 5pm - 7pm, Thursday: Potato Skins with all the fixings, free
  • 5pm - 7pm, Friday: Wings! Buffalo or Old Bay Chicken wings, free
  • Until Midnight, Friday & Saturday: Late Night Eats ~ all burgers available
  • 4pm - 10pm, Sunday: $5 Angus Beef Burger night
    This Annapolis favorite is a brew house with indoor dining in a charming tavern/pub with a dining room featuring a fireplace, perfect for fall and winter days. The Wisteria covered patio--the largest outdoor dining in Historic Annapolis--provides plenty of shade during the spring or summer and has a dog-friendly street cafĂ© (with a dog menu) for outdoor dining. Known for their unique Tavern food, 100+ beer choices, award-winning brunch, happy hour, and nightlife, Rams Head is the place for food, fun, and beer of the locals.

    Dry 85  (Limited Vegan/Vegetarian Selections)
    Whiskey & Craft Beer Restaurant & Bar
    Historic City of Annapolis
    193B Main Street
    Annapolis, MD 21401

    Happy Hour ~ 5 Days a Week, 3pm to 6pm
    • Wine of the Day & Well drink specials, $5
    • Draft of the day, $5
    • Bottled Beer, $3
    • Food specials, $5
    This is a cool, industrial vibe restaurant/bar in downtown Annapolis that has unique and varying liquor selections, events and changing menus. Live music and events happen here frequently. Follow the twitter feed or check their website for details. The happy hour menu can get the gut full. Check the website link to see what's on special.

    Red, Red Wine Bar  (No Vegan/Vegetarian* Selections)
    Wine Restaurant & Bar
    Historic City of Annapolis
    189B Main Street
    Annapolis, MD 21401

    Happy Hour ~ 5 Days a Week, 3pm to 6pm
    • White wine of the day, $5
    • Red wine of the day, $5
    • Sangria, $5
    • Draft beer of the day, $3
    • Well drinks, $5

    This intimate restaurant encourages wine sampling and mingling. Wall-to-wall wines and changing menu delights. The happy hour features cheese or seafood nibbles starting at $5. Stay over for the wine and cheese pairings that change frequently.

    *Most of the cheeses contain animal-based rennet.

    Fado's Irish Pub  (Very limited Vegan/Vegetarian Selections)
    Irish Pub
    One Park Place Annapolis, MD 21401
    (410) 626-0069

    Happy Hour ~ 6 Days a Week

    • 4pm to 7pm, Monday through Friday
    • 4pm to 12am close, Sunday
    • Taco Tuesdays
    • Wednesdays 7pm - 9pm: $3.25 pints & $12 Irish Beer Pitchers for Trivia Night
    • Thursday, Yappy Hour, 4pm to 7pm: Drink with your pet or adopt a furry friends brought by the SPCA
    • Thursday, 8pm, Game Night, $4 pints and tater tots
    The happy hour food and drink features:
    • $3.25 domestic draughts
    • $4.25 imports & craft beers
    • $5 wines
    • $6 signature cocktails
    • $6 appetizers

    Lemongrass (Vegan/Vegetarian Selections)
    167 West Street
    Annapolis, MD 21401
    (410) 280-0086

    Happy Hour ~ 6 Days a Week
    • 4pm to 5:30pm, Sunday
    • 5pm to 6:30pm, Monday to Thursday
    This uptown city of Annapolis restaurant features both indoor and outdoor dining. It is a small local place that has limited seating but worth going for happy hour, lunch or dinner.

    The happy hour is:
    • All appetizers, $5
    • All Beers, $3
    • All Wines by glass $5, by bottle $19
    • All Signature Cocktails $5, BFF Pitcher $15

    Vida Taco Bar (Vegan/Vegetarian Selections Available)
    200 Main Street,
    Annapolis, MD 21401
    Telephone: 443.837.6521

    Tuesday - Thursday: 4:30 PM - 10:00 PM
    Friday - Saturday: 11:30 AM - 11:00 PM
    Sunday: 11:30 AM - 9:00 PM
    Monday: Closed

    • Taco Tuesday – 20% Off Your Entire Check
    • Pitcher Wednesday – Pitchers of Margarita, Sangria, and Purple Drank $25 Each
    • Throw It Back Thursday – 20% Off All Tequila
    • Six Dollar Friday – Margarita, Sangria, and Purple Drank $6 Each from 11:30 AM to 5 PM
    • Bird Shot Saturday – $7 Bird Shots All Day
    • Sunday Funday – Vida Margaritas and Micheladas $6 Each All Day

    Fox's Den (Vegan/Vegetarian Selections Available)
    179B Main Street Street
    Annapolis, MD 21403

  • Happy Hour Weekdays 5:00-6:00pm: $4 off pizza/moules & frites, $3 off house cocktails, $2 off beers/wine by the glass
  • $10 Pizza Mondays: Each Monday all of our brick oven pizzas are only $10 each!
  • Wednesday Wine Night: Buy any bottle of wine and get a food item for free!

  • Surprisingly, this "premier gastropub" has something for all tastes, including vegetarian/vegan options. It's a cool, little underground pub in historic Annapolis with a cool vibe. The chef is always coming up with cool creations and they do cook-off competitions that are fun!