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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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12-22-2014

Events & Festivals

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...

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...

12-23-2014

Free World Beer Club Membership

  • Date: Started November 18, 2014 (Every Tuesday)
  • Times: Every Tuesday, All Day
  • Venue: 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 receive your name on our WBC plaque, an engraved pewter mug, a t-...

Groove Live!

Enjoy free shows and groove to funk, soul and R&B bands! Please check the Rams Head Center Stage website for this week's band! Swipe your Live! Rewards® card at the front desk and receive $5 f...

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 Tuesdays

Join Rising Star Karaoke Production by Kelley Hilderbrand on Tuesdays, starting November 4, 2014 at 9:00 p.m. in the Harbor View Room.

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: Swampcandy

Enjoy live music from Swampcandy every Tuesday in the Tavern from 10 PM to 1 AM.

Pub Quiz Night

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

Pub Trivia Night

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

Questionary Night

Come join us at Two Rivers Steak & Fish House for a Family Feud style trivia. Prizes vary and shots are given for correct answers! Two-for-one Sangria's and two-for-one burgers.

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...

12-24-2014

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...

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...

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.

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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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