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Annapolis Events & Festivals

Looking for things to do in Annapolis? Like to have fun? Like to keep busy? Like to create memories with loved ones? If so, it's time to head to our way. No matter what the season, Annapolis and the Chesapeake Bay is alive with a host of events and celebrations designed for the young and the young at heart. Whether you are outside on the water or inside one of our historic homes, there's an energy in the air here that keeps you coming back for more.

So what are you waiting for? Bring your family, invite your friends, indulge your senses. Join us for taste bud tingling events, quirky traditions, music to soothe your soul, and memories to last a lifetime.

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12-21-2014

Events & Festivals

An Irish Sunday Brunch

Join us for an assortment of delicious brunch menu items. Full menu also available. Stay a little longer to hear live Irish music from 4-8 in the pub.

Award Winning Sunday Brunch Buffet

Join us for brunch every Sunday1 voted Best Brunch by What's Up magazine 2 years in a row!

Bottomless Bloody Mary Bar

  • Date: Started November 16, 2014 (Every Sunday)
  • Times: Every Sunday, 10 AM - 2 PM
  • 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.

Football Central

Watch every Redskins or Ravens game on the big screen at Rams Head Center Stage and throughout the Casino. Enjoy all you can eat stadium style foods for only $15 in Rams Head Center Stage. Games and f...

Handel’s Messiah at St. Anne’s

The Chamber Chorus of the Annapolis Chorale and the Annapolis Chamber Orchestra return to historic St. Anne’s Church for this series of performances of Handel’s timeless masterpiece. Nothi...

Hard Travelers

Kenn Roberts, Mack Bailey, Mike Munford, Jon Glik and Ira Gitlin are The Hard Travelers. For more than 30 years The Travelers have continued to delight audiences from DC to Japan. The Hard Travelers b...

Holiday Festival of Trains & Toys

  • Date: November 28, 2014 to December 31, 2014
  • Times: Monday - Saturday, 10 a.m. to 4 p.m.; Sunday, 11 a.m. to 4 p.m.
  • Location: Baltimore & Ohio Railroad Museum

Celebrate the holiday season at Baltimore's largest holiday display of toy and model train layouts. Santa & Mrs. Claus arrive by locomotive to the Roundhouse at 10:30 a.m. Friday, November...

Holiday Lights Helicopter Tours Annnapolis

See the holiday lights the way Santa sees them! It’s family fun or a romantic evening, and we're flying our Holiday Lights tours nightly 5:30-8:30pm. Fly over “Lights on the Bay” a...

Jazz Brunch

  • Date: Started November 16, 2014 (Every Sunday)
  • Times: Every Sunday 10 AM - 2 PM, Jazz 11 AM - 2 PM
  • 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

Jazz on Sundays with Kristin Callahan

Everyone in the jazz scene today who has heard Kristin Callahan is in agreement--her voice is fresh, vibrant, and one to watch in the years to come. Kristin has that rare ability to coax listeners int...

Jolly Express Cruises

Make a Jolly Express Cruise part of your holiday traditions. Enjoy a holiday inspired cruise aboard Miss Anne decked out in her finest holiday garb. This 45 minute cruise includes hot cocoa, holiday m...

Lights on the Bay

Don't miss this spectacular drive-through holiday lights show beside the Chesapeake Bay. The event features more than 60 animated and stationary displays, including traditional Maryland-themed fav...

Live Music Sundays

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

The Nutcracker

The Nutcracker We invite you to the most famous Christmas Party of all time as you attend The Nutcracker where the possibility of dreams, the magic or Christmas and the wonder of the child merge thro...

The Nutcracker

The Nutcracker We invite you to the most famous Christmas Party of all time as you attend The Nutcracker where the possibility of dreams, the magic or Christmas and the wonder of the child merge thro...

Visit Hogshead

See, hear, and touch what life entailed for frontiersmen, colonial doctors, soldiers in the Revolutionary War, and enslaved or indentured workers. Here, you can pick up the heavy weight of a musket an...

WESTFIELD - It's Santa Time!

  • Date: November 14, 2014 to December 24, 2014
  • Times: From: 10:00 AM to 9:00 PM
  • Venue: Westfield Annapolis

Who's been naughty or nice? Come meet St. Nick and make the holidays special with Santa-and-me photos. Want to see Santa faster? Here's how: 1. Pre-order your photo package online 2. Make ...

William Paca House and Garden

  • Date: Started July 28, 2014 (Recurring daily)
  • Times: Monday through Saturday, 10:00 a.m. to 5:00 p.m. and Sunday, noon to 5:00 p.m.
  • Venue: William Paca House and Garden
  • Cost: $10 General Admission, $5 for children under 17, Free for HA members and volunteers

The William Paca House and Garden is a National Historic Landmark, restored by Historic Annapolis to its colonial-era splendor. Take some time to experience the 18th century life of lawyer, and signer...

12-22-2014

Burlesque's darlings, The World Famous Pontani Sisters, are making their way to Annapolis to warm the season with a special Christmas performance, hosting a cavalcade of burlesque and variety stars di...

Holiday Festival of Trains & Toys

  • Date: November 28, 2014 to December 31, 2014
  • Times: Monday - Saturday, 10 a.m. to 4 p.m.; Sunday, 11 a.m. to 4 p.m.
  • Location: Baltimore & Ohio Railroad Museum

Celebrate the holiday season at Baltimore's largest holiday display of toy and model train layouts. Santa & Mrs. Claus arrive by locomotive to the Roundhouse at 10:30 a.m. Friday, November...

Holiday Lights Helicopter Tours Annnapolis

See the holiday lights the way Santa sees them! It’s family fun or a romantic evening, and we're flying our Holiday Lights tours nightly 5:30-8:30pm. Fly over “Lights on the Bay” a...

Lights on the Bay

Don't miss this spectacular drive-through holiday lights show beside the Chesapeake Bay. The event features more than 60 animated and stationary displays, including traditional Maryland-themed fav...

Live Music: Tim Metz

Enjoy live music from Tim Metz every Monday on our Patio from 6-9 PM. No Cover

Navy Men's Basketball vs. Towson

  • Date: December 22, 2014
  • Times: Starting: 7:00 PM
  • Location: U.S. Naval Academy - Alumni Hall - 566 Brownson Road, Annapolis, MD 21402
  • Cost: $10/Adult, $5/Youth, $3/Promotion rate

Navy Men's Basketball team will play Towson on Monday, December 22 at Alumni Hall. Tickets are $10 Adult $5 youth $3 promotional rate.

Trivia Night at 1747 Pub at Reynolds Tavern

Think you and your friends are smart? Every Monday night come test our your ability to think on the fly and compete against other teams for prizes. Teams of 1-12 can participate; but leave your cell...

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Annapolis & Anne Arundel County Conference & Visitors Bureau

26 West Street, Annapolis, MD 21401

Phone: 410.280.0445   Fax: 410.263.9591
Toll-free from the U.S. 888.302.2852

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