EVENTS BY MONTH

  • January
    January
    January

    Get out of the chilly weather this January and enjoy the art and dining scenes in Annapolis.

    Learn More
  • February
    February
    February

    Ranked one of America’s Most Romantic Towns by Travel+Leisure Magazine, Annapolis is a great place to spend time in February.

    Learn More
  • March
    March
    March

    Winter is coming to an end, and March is a wonderful time to beat the crowds and get a taste of the unique character of Annapolis.

    Learn More
  • April
    April
    April

    Spring has arrived! Get out on the water, dine outside, join a tour, or take part in the many events happening in April.

    Learn More
  • May
    May
    May

    From Blue Angel Flight demonstrations to food-packed events, May in Annapolis is all about being outside.

    Learn More
  • June
    June
    June

    As summer rolls in, come enjoy Annapolis’ art, dining, history, on the water activities, and the many festivals and events in June.

    Learn More
  • July
    July
    July

    July's sunny weather encourages locals and visitors alike to enjoy the area’s outdoor activities, events, and festivals.

    Learn More
  • August
    August
    August

    Visiting Annapolis in August means one thing: Get out on the water! Climb aboard a sailboat or rent a kayak/paddleboard and cool off in the breeze.

    Learn More
  • September
    September
    September

    Fewer crowds and cooler weather in September makes for a perfect weekend getaway in Annapolis.

    Learn More
  • October
    October
    October

    Fall is here and so are the area’s seasonal festivals: Hayrides, haunted tours, and family-friendly events.

    Learn More
  • November
    November
    November

    Rated one of the best cities for the holidays by Travel+Leisure, Annapolis in November is a great way to kick start the season.

    Learn More
  • December
    December
    December

    With the holiday season in full swing, Annapolis is the perfect destination to find a special gift for everyone on your list.

    Learn More

CALENDAR OF EVENTS

What are your ideal travel dates?

to

Viewing all weekly happenings ( view all events )

WEEKLY HAPPENINGS (33)

entertainment while you're here

  • Live Music at Brian Boru!
    venue: Brain Boru

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

  • Happy Hour at Rams Head Dockside
    venue: Rams Head Dockside

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

  • Happy Hour at Rams Head Roadhouse
    venue: Rams Head Roadhouse

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

  • Happy Hour at Rams Head Tavern
    venue: Rams Head Tavern

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

  • Annapolis Spring Helicopter Tours
    venue: Monumental Helicopters

    Spring is in the air and take off into the air with a private helicopter tour over Annapolis with Monumental Helicopters. Explore City Dock ...

  • Colin Rowe at Blackwall Hitch
    venue: Blackwall Hitch

    Join us for a live performance from Colin Rowe on Thursday, March 23rd at 7:00pm.  ...

  • Live Music at Killarney House!
    venue: Killarney House

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

  • Art & Story Time
    venue: 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 Brian Boru!
    venue: Brain Boru

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

  • Friday Night Live!
    venue: Rams Head Center Stage

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

  • Happy Hour at Rams Head Dockside
    venue: Rams Head Dockside

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

  • Happy Hour at Rams Head Roadhouse
    venue: Rams Head Roadhouse

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

  • Happy Hour at Rams Head Tavern
    venue: Rams Head Tavern

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

  • Music: Loose Ties
    venue: Rams Head Tavern

    Join us every Friday night at 10pm for free live music with Loose Ties! ...

  • Annapolis Spring Helicopter Tours
    venue: Monumental Helicopters

    Spring is in the air and take off into the air with a private helicopter tour over Annapolis with Monumental Helicopters. Explore City Dock ...

  • Dana B at Blackwall Hitch
    venue: Blackwall Hitch

    Join us for a live performance from Dana B at 4:00PM on Friday, March 24th.  ...

  • Sly 45 at Blackwall Hitch
    venue: Blackwall Hitch

    Join us for a live performance from Sly 45 on Friday, March 24th at 9:30pm.  ...

  • Live Music at Killarney House!
    venue: 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!
    venue: Brain Boru

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

  • Annapolis Spring Helicopter Tours
    venue: Monumental Helicopters

    Spring is in the air and take off into the air with a private helicopter tour over Annapolis with Monumental Helicopters. Explore City Dock ...

  • Timmie Metz Band at Blackwall Hitch
    venue: Blackwall Hitch

    Join us for a live performance from Timmie Metz Band on Saturday, March 25th at 9:30pm.  ...

  • Bottomless Bloody Mary Bar
    venue: 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. ...

  • Jazz Brunch
    venue: Rams Head Tavern

    Join us for Brunch every Sunday from 10 AM to 2 PM and enjoy Live Jazz from 11 AM to 2 PM ...

  • Live Music Sundays at Galway Bay
    venue: Galway Bay

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

  • Award-winning Sunday Brunch
    venue: Killarney House

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

  • Award Winning Sunday Brunch Buffet
    venue: 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
    venue: Rams Head Dockside

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

  • $5 Burger Night at Rams Head Tavern
    venue: Rams Head Tavern

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

  • $5 Burger Night at Roadhouse
    venue: Rams Head Roadhouse

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

  • Sunday Brunch
    venue: Rams Head Dockside

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

  • Smooth Sundays
    venue: Rams Head Center Stage

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

  • Annapolis Spring Helicopter Tours
    venue: Monumental Helicopters

    Spring is in the air and take off into the air with a private helicopter tour over Annapolis with Monumental Helicopters. Explore City Dock ...

  • Jazz Brunch at Blackwall Hitch
    venue: Blackwall Hitch

    Join us Sunday, March 26th for Brunch and a live performance from Sly 45 at 10:00am.  ...