USNA Commissioning Week: Annapolis Food & Entertainment Guide

May 2, 2022

The countdown for Commissioning Week at the United States Naval Academy is on! Starting Friday, May 20, exciting commissioning events return for an entire week, including our favorite, the Blue Angels Flight Demonstrations. These week-long celebrations lead up to the commencement ceremony at Navy-Marine Corps Memorial Stadium on Friday, May 27, with a speech by President Joe Biden. For a complete schedule of USNA events, click here.


When you’re not occupied with commissioning week activities, you’ll probably be looking for other things to do, places to see and great things to eat here in Annapolis. While Maryland is known for “crab cakes and football” (and we have both), we can assure you that there’s much more our town has to offer.


Below is our guide to navigating the Annapolis food and entertainment scene like a local.


Dining (* = we recommend making a reservation):

  • Chart House* – located just over the Eastport bridge, this fine dining establishment offers a dazzling view of downtown Annapolis on the water. Be sure to book a reservation ASAP as it is one of the more popular restaurants around.
  • Carpaccio Tuscan Kitchen & Wine Bar* – located next door to the Westin Hotel, you will find some of the best Italian cuisine in the area.
  • Light House Bistro – nestled in the center of West St., the Light House Bistro offers polished American cuisine for breakfast and lunch. This establishment was created in partnership with the Light House Homeless Prevention Center to give people with employment barriers the opportunity to learn while developing a resume and earning a living wage.
  • Sailor Oyster Bar – committed to creating a surreal dining experience, Sailor Oyster Bar features delicious seafood dishes and fantastic daily specials. Word to the wise: check out their Instagram account for daily specials and menu changes!
  • Bread & Butter Kitchen – a personal favorite of Liquified Creative! This café offers fresh and delicious options for breakfast and lunch daily, along with great waterfront views.
  • Chick & Ruth’s Delly – an Annapolis staple located on the heart of Main St., Chick & Ruth’s offers just about everything you want. For those who are daring, try the Man vs. Food Challenge – a 6lb milkshake and a 3lb burger!
  • Pusser’s Caribbean Grill – a Jamaican-inspired waterfront restaurant & bar in Ego Alley, Pusser’s offers the quintessential Annapolis outdoor dining experience.
  • McGarvey’s – a cornerstone of Annapolis located down by the City Dock, McGarvey’s offers the freshest seafood, a friendly atmosphere, and a memorable experience.
  • Dinner Under the Stars – an experience unlike any other! Dinner Under the Stars brings together music and cuisine from five restaurants in an outdoor setting every Wednesday. Be advised – inclement weather means the outdoor portion of this will be canceled, so be sure to have a backup plan just in case (you can still dine at each of the participating restaurants: Rams Head Tavern, Luna Blu, Tsunami Sushi Bar and Lounge, Stan & Joe’s Saloon, and 49 West Coffeehouse Winebar & Gallery).



  • Rams Head on Stage – Rams Head on Stage is your premier concert venue in downtown Annapolis, with performances from national acts. Don’t miss The Wallflowers on Tuesday, May 24!
  • GameOn Bar+Arcade – Be sure to swing by Annapolis’ newest entertainment emporium, complete with vintage arcade games, pinball, Pac-Man, skeeball, and more!
  • Mission Escape Room – Do you have what it takes to escape? Located on West St, Mission Escape Room tests your group’s ability to escape a locked room using clues and solving puzzles. Fun for the whole family!
  • Annapolis Maritime Museum – Learn about Annapolis’ rich maritime history and the ecology of the Chesapeake Bay. Book a sailboat ride aboard the Wilma Lee, one of 23 remaining Chesapeake Skipjacks, and explore Annapolis and the Chesapeake Bay.
  • Quiet Waters Park – Explore 340 acres of nature, including trails, playgrounds, and pavilions that are perfect for any picnic. Quiet Waters Park is open seven days a week from 7am until dusk and requires an entry fee of $6 (cash only).
  • Banneker-Douglass Museum – Located just off of Church Circle, this museum is dedicated to documenting, interpreting, and promoting African-American history and culture in Maryland through exhibitions, programs, and projects.
  • William Paca House & Garden – Built by one of Maryland’s four Signers of the Declaration of Independence, this restored 18th-century mansion offers guests insights into the inner workings of an upper-class household in colonial and revolutionary Annapolis.
  • Maryland Ave. – A whole street full of hidden gems right off State Circle. Maryland Avenue offers boutique shops & restaurants that will delight your soul.


Graduation may only last a couple of hours, but the memories made during Commissioning Week will last a lifetime.


Liquified Creative would like to extend a warm congratulations and best wishes to the USNA Class of 2022 as they move up the ranks! As we join the rest of Annapolis in celebrating this year’s graduating class of the United States Naval Academy, we’re proud to release our annual USNA Commissioning Week Screensavers (desktop + mobile), which can be downloaded below.

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