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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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12-17-2014

Events & Festivals

Drawing and Painting the Life at Maryland Hall

Over the past two years artist, Andrée Tullier, has been creating genre works featuring the Life at Maryland Hall. Combining pastel, oil, and charcoal, this solo-exhibition embraces the endeavo...

Holiday Candlelight Stroll

  • Date: December 05, 2014 to December 20, 2014
  • Times: From: 7:00 PM to 8:00 PM
  • Location: Tours depart from the Information Booth at City Dock
  • Cost: $16 adults, $12 children under 12

Learn about the origin of holiday traditions - including the significance of evergreens, Yule logs, Christmas trees, and Santa Claus. The stroll along festive Annapolis streets is a perfect way to g...

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...

Karaoke Live!

  • Date: Started November 12, 2014 (Every Wednesday)
  • Times: Starting: 8:00 PM
  • Venue: Rams Head Center Stage
  • Cost: $5 at the door

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 on a first come first serve basis.

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: Dean Rosenthal

Join us every Wednesday 5 - 8 PM on the patio for live music from Dean Rosenthal.

Pieces of a Dream

You get the best of Jazz and R&B in one great show! Pieces of a Dream emerged out of Philadelphia's music scene in 1976. Long before the "Young Lions" era of Wynton Marsalis, James Lloyd...

Trivia Night at Two Rivers Steak & Fish House

Join us every Wednesday night for Charm City Trivia. Have a chance to win shots and prizes such as a $15 Two Rivers gift card. Enjoy a half priced bottle of select wines every Wednesday!

US Naval Academy Band - "Holiday by the Bay" concert

Join the Naval Academy Band for a favorite Annapolis tradition: "Holiday by the Bay". The concert features the Brass Ensemble and will take place on Wednesday, December 17 at 7:30 p.m. on t...

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...

12-18-2014

11th Hour Downtown

  • Date: December 18, 2014
  • Times: Ending: 11:00 PM
  • Location: Maryland Avenue/State Circle Shopping District/Downtown Annapolis Shopping District

If shoppers didn't purchase all of their holiday gifts at Midnight Madness.  11th Hour gives them one more opportunity to check names off their gift list.  Shops stay open until 11:00 p.m....

Hack and Slash Christmas Show

Baltimore's most popular Christmas comedy event is back! Join Spencer "Slash" Humm, the Christmas Ninjas, many of your favorite performers from Christmas Specials past and, a few talented an...

Holiday Candlelight Stroll

  • Date: December 05, 2014 to December 20, 2014
  • Times: From: 7:00 PM to 8:00 PM
  • Location: Tours depart from the Information Booth at City Dock
  • Cost: $16 adults, $12 children under 12

Learn about the origin of holiday traditions - including the significance of evergreens, Yule logs, Christmas trees, and Santa Claus. The stroll along festive Annapolis streets is a perfect way to g...

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 at Brian Boru!

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

Live Music: Pressing Strings

Enjoy live music from Pressing Strings every Thursday in the Tavern from 10 PM to 1 AM

Open Mic Night

Come join us at Two Rivers Steak & Fish House for a night of fun and chance to show off your talents! Whatever your talent may be, such as singing, comedy, poetry, or event playing a instrument, w...

Robert Randolph & The Family Band

When Robert Randolph talks about his new album, Lickety Split, a few words come up over and over—"joy," "freedom," "energy." Which is no surprise, really, because t...

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...

12-19-2014

Art & Story Time

We are eager to share the passion for great children's literature and creative visual expression with our youngest visitors. Children ages two to five years old and their accompanying adults can share...

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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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