WEEKLY HAPPENINGS (114)

entertainment while you're here

Happy Hour at Rams Head Tavern
Rams Head Tavern

Happy Hour is every Monday through Friday from 3-7pm! ...

Pub Quiz Night at Galway Bay
Galway Bay

Pub Quiz night. Registration starts at 7:30. Teams compete to answer rounds of trivia questions. Winning team wins prize and chooses a chari ...

Pub Trivia Night at Brian Boru
Brian Boru

Pub Trivia in 3 rounds with prizes for the winners! 7-9pm Bring a team and have some fun! ...

Happy Hour at Rams Head Roadhouse
Rams Head Roadhouse

Happy Hour is every Monday through Friday from 3-7pm! ...

Live Music at Rams Head Roadhouse
Rams Head Roadhouse

Free live music every Tuesday at 7:30PM! ...

Free World Beer Club Membership
Rams Head Tavern

Join our World Beer Club for free on Tuesdays. As a member you will be sample 100 beer from around the world. Upon completion you will recei ...

Happy Hour at Rams Head Dockside
Rams Head Dockside

Happy Hour is every Monday through Friday from 3-7pm! ...

Four Centuries Walking Tour at 1:30 PM
Watermark Tours, Charters, Cruises

A colonial attired tour guide brings history to life as you visit key sites – including the Maryland State House and the U.S. Naval Aca ...

Four Centuries Walking Tour at 10:30 AM
Watermark Tours, Charters, Cruises

A colonial attired tour guide brings history to life as you visit key sites – including the Maryland State House and the U.S. Naval Aca ...

Happy Hour
Yellowfin Steak & Fish House

Best Happy Hour in Town 4pm to 7pm Everyday Happy Hour menus starting at $4. ...

Sunday Brunch
Yellowfin Steak & Fish House

Sunday Brunch Enjoy unlimited MImosas, made to order omletes and more, all while overlooking the beautiful south river. ...

Taco Tuesdays
Rico's Taco and Tequila Bar

ALL TACOS $3.00 ALL DAY! ...

Happy Hour and Half Shell
Sailor Oyster Bar

$1 Local Oysters / Beer & Wine Special ...

TuneUp Tuesdays
Live! Center Stage

You pick it, we play it. Hand in your song request and watch dueling pianos like you never seen before, as a part of a 5-piece party band. B ...

Happy Hour
Ashling Kitchen & Bar

50% Off Small Plates and $2 Off Drinks ...

Annapolis Bar & Grill Date Night Special!
Crowne Plaza Annapolis

Two surf and turf entrees with your choice of grilled gulf shrimp or lump crab cake with a 6oz filet., accompanied by your choice of any bot ...

Daily Sailing on the Chesapeake Bay
Annapolis Sailing Cruises: Schooner Woodwind

Help raise the sails, steer the boat or just sit back and relax aboard the Schooner Woodwind. Sail times are 12:30-2:30, 3:00-5:00, & 5 ...

Annapolis Harbor & US Naval Academy Cruise
Watermark Tours, Charters, Cruises

A must-do Annapolis activity! Step aboard Harbor Queen for a narrated cruise of historic Annapolis Harbor and the banks of the U.S. Naval Ac ...

Tuesday Beer Tasting Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Sample while you sail!  A representative from Union Craft Brewing in Baltimore, MD comes aboard and teaches you about their beer. 3 samp ...

Happy Hour at Rams Head Tavern
Rams Head Tavern

Happy Hour is every Monday through Friday from 3-7pm! ...

Karaoke Live!
Live! Center Stage

Take Center Stage and be the star of the show at Karaoke Live! Sing your favorite songs with a live band to back you up! Seating available o ...

Live Music with Sean Hetrick and $6 Burgers
Reynolds Tavern

Join us for a great Wednesday night of music and $6 burgers, inside the 1747 Pub at Reynolds Tavern.  Listen to live music by Sean Hetrick ...

Amber North
Rams Head Tavern

Join us every Wednesday night for live music with Amber North! No cover! ...

Happy Hour at Rams Head Roadhouse
Rams Head Roadhouse

Happy Hour is every Monday through Friday from 3-7pm! ...

Live Music at Rams Head Dockside
Rams Head Dockside

Join us every Wednesday, Friday, and Saturday evening for free live music! No cover!  ...

Happy Hour at Rams Head Dockside
Rams Head Dockside

Happy Hour is every Monday through Friday from 3-7pm! ...

Four Centuries Walking Tour at 1:30 PM
Watermark Tours, Charters, Cruises

A colonial attired tour guide brings history to life as you visit key sites – including the Maryland State House and the U.S. Naval Aca ...

Four Centuries Walking Tour at 10:30 AM
Watermark Tours, Charters, Cruises

A colonial attired tour guide brings history to life as you visit key sites – including the Maryland State House and the U.S. Naval Aca ...

Wednesday Night Races
Annapolis Sailing Cruises: Schooner Woodwind

Woodwind and Woodwind II will be match racing every Wednesday night that there is an Annapolis Yacht Club (AYC) Race. Both boats will sta ...

Happy Hour
Yellowfin Steak & Fish House

Best Happy Hour in Town 4pm to 7pm Everyday Happy Hour menus starting at $4. ...

Sunday Brunch
Yellowfin Steak & Fish House

Sunday Brunch Enjoy unlimited MImosas, made to order omletes and more, all while overlooking the beautiful south river. ...

Happy Hour and Half Shell
Sailor Oyster Bar

$1 Local Oysters / Beer & Wine Special ...

Karaoke with KJ Billy
Rams Head Dockside

Join us every Wednesday for karaoke with one of Glen Burnie's favorites, KJ Billy! As always, no cover. Happy Hour: 3 to 7 1/2 price apps ...

Happy Hour
Ashling Kitchen & Bar

50% Off Small Plates and $2 Off Drinks ...

Annapolis Bar & Grill Date Night Special!
Crowne Plaza Annapolis

Two surf and turf entrees with your choice of grilled gulf shrimp or lump crab cake with a 6oz filet., accompanied by your choice of any bot ...

Daily Sailing on the Chesapeake Bay
Annapolis Sailing Cruises: Schooner Woodwind

Help raise the sails, steer the boat or just sit back and relax aboard the Schooner Woodwind. Sail times are 12:30-2:30, 3:00-5:00, & 5 ...

Annapolis Harbor & US Naval Academy Cruise
Watermark Tours, Charters, Cruises

A must-do Annapolis activity! Step aboard Harbor Queen for a narrated cruise of historic Annapolis Harbor and the banks of the U.S. Naval Ac ...

Happy Hour at Rams Head Tavern
Rams Head Tavern

Happy Hour is every Monday through Friday from 3-7pm! ...

Music: Pete Best
Rams Head Tavern

Join us every Thursday night for live music with Pete Best No cover! ...

Live Music at Brian Boru!
Brain Boru

Live music Thursday, Friday and Saturday nights, year round! ...

1/2 Price Maison Nicolas Wines
Reynolds Tavern

Every Thursday Night enjoy 1/2 Price bottles of Maison Nicolas Wines with food purchase.  Pinot Grigio, Chardonnay, Sauvignon Blanc, Merlot ...

Happy Hour at Rams Head Roadhouse
Rams Head Roadhouse

Happy Hour is every Monday through Friday from 3-7pm! ...

Happy Hour at Rams Head Dockside
Rams Head Dockside

Happy Hour is every Monday through Friday from 3-7pm! ...

Four Centuries Walking Tour at 1:30 PM
Watermark Tours, Charters, Cruises

A colonial attired tour guide brings history to life as you visit key sites – including the Maryland State House and the U.S. Naval Aca ...

Four Centuries Walking Tour at 10:30 AM
Watermark Tours, Charters, Cruises

A colonial attired tour guide brings history to life as you visit key sites – including the Maryland State House and the U.S. Naval Aca ...

Happy Hour
Yellowfin Steak & Fish House

Best Happy Hour in Town 4pm to 7pm Everyday Happy Hour menus starting at $4. ...

Sunday Brunch
Yellowfin Steak & Fish House

Sunday Brunch Enjoy unlimited MImosas, made to order omletes and more, all while overlooking the beautiful south river. ...

Ladies' Night
Rico's Taco and Tequila Bar

Ladies Night 1/2 off house drinks all day! ...

Happy Hour and Half Shell
Sailor Oyster Bar

$1 Local Oysters / Beer & Wine Special ...

Trivia with DJ Matt
Rams Head Dockside

Join us for Trivia every Thursday starting at 8 PM! Specials: $7 Domestic pitchers, $10 Fordham & Dominion pitchers Winning team take ...

Happy Hour
Ashling Kitchen & Bar

50% Off Small Plates and $2 Off Drinks ...

Annapolis Bar & Grill Date Night Special!
Crowne Plaza Annapolis

Two surf and turf entrees with your choice of grilled gulf shrimp or lump crab cake with a 6oz filet., accompanied by your choice of any bot ...

Daily Sailing on the Chesapeake Bay
Annapolis Sailing Cruises: Schooner Woodwind

Help raise the sails, steer the boat or just sit back and relax aboard the Schooner Woodwind. Sail times are 12:30-2:30, 3:00-5:00, & 5 ...

Annapolis Harbor & US Naval Academy Cruise
Watermark Tours, Charters, Cruises

A must-do Annapolis activity! Step aboard Harbor Queen for a narrated cruise of historic Annapolis Harbor and the banks of the U.S. Naval Ac ...

Thursday Acoustic Music Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Sit back and relax as Deanna Dove entertains you while sailing on the Chesapeake Bay. The cruise departs from the Annapolis Waterfront Hot ...

Happy Hour at Rams Head Tavern
Rams Head Tavern

Happy Hour is every Monday through Friday from 3-7pm! ...

Art & Story Time
Chesapeake Children's Museum

We are eager to share the passion for great children's literature and creative visual expression with our youngest visitors. Children ages t ...

Live Music at Killarney House!
Killarney House

Live music Every Friday and Saturday night at Killarney House. go to our website for current artist listings and schedules. ...

Friday Night Live!
Live! Center Stage

Friday Night Live! Join us for a night of fun and live entertainment as we bring you the top requested music at Live! Center Stage! 1st Fr ...

Live Music at Brian Boru!
Brain Boru

Live music Thursday, Friday and Saturday nights, year round! ...

Happy Hour at Rams Head Roadhouse
Rams Head Roadhouse

Happy Hour is every Monday through Friday from 3-7pm! ...

Live Music at Rams Head Dockside
Rams Head Dockside

Join us every Wednesday, Friday, and Saturday evening for free live music! No cover!  ...

Happy Hour at Rams Head Dockside
Rams Head Dockside

Happy Hour is every Monday through Friday from 3-7pm! ...

Four Centuries Walking Tour at 1:30 PM
Watermark Tours, Charters, Cruises

A colonial attired tour guide brings history to life as you visit key sites – including the Maryland State House and the U.S. Naval Aca ...

Four Centuries Walking Tour at 10:30 AM
Watermark Tours, Charters, Cruises

A colonial attired tour guide brings history to life as you visit key sites – including the Maryland State House and the U.S. Naval Aca ...

Happy Hour
Yellowfin Steak & Fish House

Best Happy Hour in Town 4pm to 7pm Everyday Happy Hour menus starting at $4. ...

Sunday Brunch
Yellowfin Steak & Fish House

Sunday Brunch Enjoy unlimited MImosas, made to order omletes and more, all while overlooking the beautiful south river. ...

Late Night Happy Hour!
Rico's Taco and Tequila Bar

Late Night Happy Hour! From 9PM-11PM Fridays and Saturdays ...

Happy Hour and Half Shell
Sailor Oyster Bar

$1 Local Oysters / Beer & Wine Special ...

Ladies Night with DJ Matt
Rams Head Dockside

Get the girls together because it's Ladies Night! Join us every Friday starting at 9pm for Ladies Night with DJ Matt. Enjoy $3 bombs, $3 ...

Happy Hour
Ashling Kitchen & Bar

50% Off Small Plates and $2 Off Drinks ...

Annapolis Bar & Grill Date Night Special!
Crowne Plaza Annapolis

Two surf and turf entrees with your choice of grilled gulf shrimp or lump crab cake with a 6oz filet., accompanied by your choice of any bot ...

Daily Sailing on the Chesapeake Bay
Annapolis Sailing Cruises: Schooner Woodwind

Help raise the sails, steer the boat or just sit back and relax aboard the Schooner Woodwind. Sail times are 12:30-2:30, 3:00-5:00, & 5 ...

Annapolis Harbor & US Naval Academy Cruise
Watermark Tours, Charters, Cruises

A must-do Annapolis activity! Step aboard Harbor Queen for a narrated cruise of historic Annapolis Harbor and the banks of the U.S. Naval Ac ...

Historic Ghost Walk
Watermark Tours, Charters, Cruises

Haunted ghost tour at night with period dressed guides. Led by candlelight through historic Annapolis. Learn the city's most chilling tales. ...

Live Music at Killarney House!
Killarney House

Live music Every Friday and Saturday night at Killarney House. go to our website for current artist listings and schedules. ...

Live Music at Brian Boru!
Brain Boru

Live music Thursday, Friday and Saturday nights, year round! ...

Live Music at Rams Head Dockside
Rams Head Dockside

Join us every Wednesday, Friday, and Saturday evening for free live music! No cover!  ...

Four Centuries Walking Tour at 1:30 PM
Watermark Tours, Charters, Cruises

A colonial attired tour guide brings history to life as you visit key sites – including the Maryland State House and the U.S. Naval Aca ...

Four Centuries Walking Tour at 10:30 AM
Watermark Tours, Charters, Cruises

A colonial attired tour guide brings history to life as you visit key sites – including the Maryland State House and the U.S. Naval Aca ...

Day on the Bay to St. Michaels
Watermark Tours, Charters, Cruises

Cruise across the Bay to spend over three hours at this quaint, historic village, enjoying fresh seafood, boutique shopping and historic sit ...

Happy Hour
Yellowfin Steak & Fish House

Best Happy Hour in Town 4pm to 7pm Everyday Happy Hour menus starting at $4. ...

Sunday Brunch
Yellowfin Steak & Fish House

Sunday Brunch Enjoy unlimited MImosas, made to order omletes and more, all while overlooking the beautiful south river. ...

Saturday Wine Tastings
Wine Cellars of Annapolis

Join us every Saturday from 11:00am-4:00pm for exciting Wine Tastings in our Barrel Room where we feature a variety of great wines with ...

Late Night Happy Hour!
Rico's Taco and Tequila Bar

Late Night Happy Hour! From 9PM-11PM Fridays and Saturdays ...

Margarita Madness!
Rico's Taco and Tequila Bar

Margarita Madness $6 House Margaritas! From 2PM-4PM Saturdays ...

Happy Hour and Half Shell
Sailor Oyster Bar

$1 Local Oysters / Beer & Wine Special ...

Annapolis Bar & Grill Date Night Special!
Crowne Plaza Annapolis

Two surf and turf entrees with your choice of grilled gulf shrimp or lump crab cake with a 6oz filet., accompanied by your choice of any bot ...

Daily Sailing on the Chesapeake Bay
Annapolis Sailing Cruises: Schooner Woodwind

Help raise the sails, steer the boat or just sit back and relax aboard the Schooner Woodwind. Sail times are 12:30-2:30, 3:00-5:00, & 5 ...

Historic Ghost Walk
Watermark Tours, Charters, Cruises

Haunted ghost tour at night with period dressed guides. Led by candlelight through historic Annapolis. Learn the city's most chilling tales. ...

Chesapeake Bay Bridges Cruise
Watermark Tours, Charters, Cruises

Marvel at the engineering feat as you cruise under the twin spans of the Bay Bridges that connect the eastern and western shores of Maryland ...

Scenic Severn River Cruise
Watermark Tours, Charters, Cruises

A spectacular 6-mile cruise on the beautiful scenic Severn River. View the historic Annapolis Harbor including the banks of the U.S. Naval A ...

Thomas Point Lighthouse Cruise
Watermark Tours, Charters, Cruises

One of the most recognized lighthouses in Maryland, view this National Historic Landmark while cruising the Chesapeake Bay. Beer, Wine, mixe ...

Music: Skribe
Rams Head Tavern

Join us every Sunday night for live music with Skribe! No cover! ...

$5 Burger Night at Rams Head Tavern
Rams Head Tavern

Serving up delicious burgers every Sunday night for just $5! ...

Award-winning Sunday Brunch at Killarney House
Killarney House

Join us every Sunday for our award-winning Sunday Brunch featuring breakfast favorites plus Irish specialties from our kitchen! 10-2pm Every ...

Live Music Sundays at Galway Bay
Galway Bay

Join us for live Irish music every Sunday from 4-8pm in the pub! ...

Smooth Sundays
Live! Center Stage

Smooth Sundays Ease into the week with martinis and Jazz Music on Sundays from 6:00PM - 9:00PM ...

Award Winning Sunday Brunch Buffet at Brian Boru
Brian Boru

Join us for brunch every Sunday! Voted Best Brunch by What's Up Magazine 2 years in a row! ...

$5 Burger Night at Rams Head Dockside
Rams Head Dockside

Serving up delcious burgers for just $5 every Sunday from 4-10pm! ...

$5 Burger Night at Rams Head Roadhouse
Rams Head Roadhouse

Serving up delicious burgers every Sunday night for just $5 from 4-10pm! ...

Bottomless Bloody Mary Bar at Rams Head Tavern
Rams Head Tavern

We provide the fixin's, you provide the mixin'! Enjoy $10 Finlandia Bottomless Bloody Mary Bar with the purchase of an entree. ...

Sunday Brunch at Rams Head Dockside
Rams Head Dockside

Join us for Brunch every Sunday from 10 AM to 2 PM! ...

Four Centuries Walking Tour at 1:30 PM
Watermark Tours, Charters, Cruises

A colonial attired tour guide brings history to life as you visit key sites – including the Maryland State House and the U.S. Naval Aca ...

Four Centuries Walking Tour at 10:30 AM
Watermark Tours, Charters, Cruises

A colonial attired tour guide brings history to life as you visit key sites – including the Maryland State House and the U.S. Naval Aca ...

Free Outdoor Movie Screenings
Reynolds Tavern

First of all, who doesn’t love a Free Movie Screening? Add the fact that it is outside under the beautiful Annapolis sky, and you autom ...

Happy Hour
Yellowfin Steak & Fish House

Best Happy Hour in Town 4pm to 7pm Everyday Happy Hour menus starting at $4. ...

Sunday Brunch
Yellowfin Steak & Fish House

Sunday Brunch Enjoy unlimited MImosas, made to order omletes and more, all while overlooking the beautiful south river. ...

Happy Hour and Half Shell
Sailor Oyster Bar

$1 Local Oysters / Beer & Wine Special ...

Daily Sailing on the Chesapeake Bay
Annapolis Sailing Cruises: Schooner Woodwind

Help raise the sails, steer the boat or just sit back and relax aboard the Schooner Woodwind. Sail times are 12:30-2:30, 3:00-5:00, & 5 ...

Chesapeake Bay Bridges Cruise
Watermark Tours, Charters, Cruises

Marvel at the engineering feat as you cruise under the twin spans of the Bay Bridges that connect the eastern and western shores of Maryland ...

Scenic Severn River Cruise
Watermark Tours, Charters, Cruises

A spectacular 6-mile cruise on the beautiful scenic Severn River. View the historic Annapolis Harbor including the banks of the U.S. Naval A ...

Thomas Point Lighthouse Cruise
Watermark Tours, Charters, Cruises

One of the most recognized lighthouses in Maryland, view this National Historic Landmark while cruising the Chesapeake Bay. Beer, Wine, mixe ...

Annapolis Harbor & US Naval Academy Cruise
Watermark Tours, Charters, Cruises

A must-do Annapolis activity! Step aboard Harbor Queen for a narrated cruise of historic Annapolis Harbor and the banks of the U.S. Naval Ac ...