Annapolis is home to incredible arts and culture scenes, outstanding and diverse dining options, and a rich, storied history. It’s also home to three of the nation’s largest boat shows — the U.S. Power Boat Show (Oct. 3-6, 2019), the U.S. Sailboat Show (Oct. 10-14), and the Annapolis Spring Sailboat Show (April).

If you’re visiting the Sailing Capital of the U.S., Annapolis, for one of this season’s boat shows, you’ll want to experience the city like a local! Be sure to make these seven stops during your time in Maryland’s capital this fall.

Photo courtesy: Visit Annapolis

1. Catch a show at Rams Head On Stage

Rams Head On Stage has been named by Pollstar as the World’s Top Music Club Under 500 Seats! This intimate, eclectic venue welcomes national and international entertainers for concerts and performances by chart-topping musicians, nationally known comedians, up-and-coming local and regional artists, top-of-the-line tribute acts, and more. Coming soon to Rams Head:

OCTOBER 4-7, 2019

Friday, October 4 at 8pm | The Doobie Others: A Tribute To The Doobie Brothers | Tickets $29.50
Saturday, October 5 at 1pm | Mason Jennings – All-Ages Matinee | Tickets $25
Saturday, October 5 at 8pm | Technicolor Motor Home: A Steely Dan Tribute | Tickets $28.50
Sunday, October 6 at 7:30pm | Rams Head Presents Blue Oyster Cult at Maryland Hall for the Creative Arts | Tickets $55-80
Sunday, October 6 at 8pm | Langhorne Slim & The Lost At Last Band with Katie Pruitt | Tickets $39.50

OCTOBER 10-14, 2019

Thursday, October 10 at 8pm | Renaissance | Tickets $39.50
Friday, October 11 at 5pm and 8pm | Phil Vassar: Hitsteria Tour | Tickets $49.50
Saturday, October 12 at 1pm | Johnny A. & Kasim Sulton: Songs & Stories – All-Ages Matinee | Tickets $35
Saturday, October 12 at 8pm | Jimmie Vaughan | Tickets $47.50
Sunday, October 13 at 8pm | Tiffany | Tickets $46.50
Monday, October 14 at 8pm | Steven Page Trio Formerly of Barenaked Ladies with Dean Friedman | Tickets $27.50

Click here to view Rams Head On Stage’s full calendar of upcoming shows.

2. Check out happy hour at Rams Head Tavern Annapolis

If you’re looking for a delicious cocktail at a great price on a beautiful, fall evening, Rams Head Tavern Annapolis is the place to go. Enjoy one of the area’s best happy hours, offered Monday through Friday from 3 to 7pm. Rams Head Tavern is located at 33 West Street, Annapolis, MD 21401

Happy Hour:
1/2 Price Appetizers
$2 OFF Wine & Liquor
$3 Draft Beer
$2.5 Domestic Bottles
Happy hour specials are offered Monday through Friday from 3pm to 7pm.

3. Stroll West Street at the First Sunday Arts Festival

The First Sunday Arts Festival connects Annapolitans and visitors with local businesses, community organizations, artisans, musicians, and other vendors for a full day of great sounds, great sights, and great smells! The festival takes place throughout downtown Annapolis’ Calvert and West Streets on the first Sunday of each month from May to November. Take this cultural stroll during their October festival on October 6 from 11am to 5pm.

4. Enjoy a great meal at Rams Head

Whether you’re only in town for two days or you’re turning the boat show into an excuse for a relaxing, fun, long weekend, be sure to take advantage of Rams Head’s robust selection of appetizers, entrees, salads, sandwiches, and more! View their full menu here. Or, try one of their daily or weekly special to get a deal that will make you want to visit Annapolis all the time!

Weekly Specials:
Sunday | Sunday Jazz Brunch, Bottomless Bloody Mary Bar ($10 with entree purchase), $5 Burger Night
Monday | Lobster Night ($22.95)
Tuesday | Prime Rib Night ($14.95/$16.95)
Wednesday | Kids Eat Free (Prices vary)
Thursday | Taco Thursday ($2.75 street tacos, $3.95 margaritas, and more!)

6. Go to a Navy football game

Support the U.S. Naval Academy’s football team as they take on the U.S. Air Force Falcons on Saturday, October 5 at 3:30pm at Navy-Marine Corps Stadium here in Annapolis. No matter who you’re rooting for, the Navy-Air Force matchup is always a sight to behold.

7. Cheer on your favorite NFL team 

Catch Ravens or Redskins games at Rams Head Tavern, while taking full advantage of their game-winning NFL specials! These specials are available on Sundays, Mondays, and Thursdays starting one hour before kickoff, only in the Tavern and Pub areas:

NFL Specials
$3 Fordham & Dominion drafts
$3 OFF all appetizers
$12 Buckets (5 bottles: Budweiser, Bud Light, Miller Lite, Coors Light, or Michelob Ultra)