Annapolis, Maryland—Visit Annapolis & Anne Arundel County (VAAAC) wants to make it easy for visitors and area residents to enjoy the many exciting events and activities that will be taking place in Annapolis and Anne Arundel County throughout 2019. To assist individuals who are making advance plans for business or vacation travel, VAAAC has put together a 2019 Major Events Calendar. For a more comprehensive overview of events large and small, visit http://www.visitannapolis.org. Events are subject to change without notice. Please call ahead to verify dates and times.

January

Ten-thousand plungers take an icy dip in the Chesapeake Bay to raise money for Special Olympics Maryland in the Polar Bear Plunge. January 24-26. www.plungemd.com

March

Nine days, two weekends, 40+ restaurants offering price fixed menus during Annapolis Restaurant Week. March 2-10. www.downtownannapolispartnership.org/restaurant-week.

Celebrate all things Irish – complete with Irish bands, food and a grand parade during the Annapolis Hooley Celebration and St. Patrick’s Parade. March 9-10. www.naptownevents.com

The 7th Annual Annapolis Film Festival features more than 70 films in all genres from around the globe – some airing for the first time.March 21-24. www.annapolisfilmfestival.com

Celebrate the arrival of spring in true Annapolis style at the 9th Annual Annapolis Oyster Roast & Sock Burning. March 23. https://amaritime.org/event/annapolis-oyster-roast-sock-burning

Discover Annapolis and Southern Anne Arundel County’s cultural and heritage sites for one-dollar or less per attraction during the 12th Annual Maryland Day. March 29-31. www.marylandday.org

April

The Annapolis Book Festival celebrates the beauty, power, passion and excitement of the written word through new and used book sales, signings and panels featuring nationally renowned authors. April 6. https://www.keyschool.org/community/annapolis-book-festival

Some 130 crews race around markers in the Chesapeake Bay delighting onlookers weekly throughout the summer in the Wednesday Night Sailboat Races. Tentative start and end dates: April 24 through August 28. www.annapolisyc.com

The 8th Annual Annapolis Spring Sailboat Show provides many experienced and novice sailors with their first yearly opportunity to shop for the latest in equipment, high-tech electronics, inflatables, clothing, boating accessories, gear and related services at the show’s 100+ on-land nautical exhibits and on-site pro surf shops. April 26-28.  http://www.annapolisboatshows.com/annapolis-spring-sailboat-show

The inaugural Boat Maryland Week Celebration offers fun events, informative classes and exhibits celebrating the area’s Maritime Heritage. April 26-May 5. http://www.boatmarylandweek.com.

37th Annual Annapolis Cup Croquet Match: St. John’s College vs. U.S. Naval Academy is an annual rite of spring that brings together two vastly different schools for a croquet match like no other. April 27, rain or shine. sjc.edu/croquet

May

Some would say May Day is the most beautiful day in Annapolis! Come, camera in hand, to capture door after door of baskets filled with colorful spring flowers during the 63rdAnnual May Day Basket Competition. May 1. http://www.downtownannapolispartnership.org/may-day-baskets

Some 130 crews race around markers in the Chesapeake Bay delighting onlookers weekly throughout the summer in the Wednesday Night Sailboat Races. Wednesdays, May 1 through August 28. www.annapolisyc.com

Shop among the creations of 130 local and regional artisans; dine at outdoor cafes; and enjoy the music of more than seven live bands each day during the 17th Annual First Sunday Arts Festival. May 5 and every first Sunday of the month through November 3. www.firstsundayarts.com

After four years of 24/7 work, dedication and commitment, graduating midshipmen receive their commissions as officers in the U.S. Navy and Marine Corps during the grand finale of U.S. Naval Academy Commissioning Week. The weeklong celebration includes concerts, a formal parade, the Herndon Monument climb, and a Blue Angels flight demonstration. Tentative dates: May 17-May 24. https://www.usna.edu/CommissioningWeek/index.php

Celebrate the men and women who made the ultimate sacrifice for our country at the Annapolis Memorial Day Parade. May 27. www.annapolis.gov

Capture a taste of Athens right here in Annapolis at the Annapolis Greek Festival. May 30-June 2. www.annapolisgreekfestival.org

June

All levels of paddlers come together for a day of camaraderie as they experience the thrill of paddling the Chesapeake Bay during the 4th Annual Bay Bridge Paddle. June 1. http://abceventsinc.com/bay-bridge-paddle

Capture a taste of Athens right here in Annapolis at the Annapolis Greek Festival. June 1-2. www.annapolisgreekfestival.org

Annapolis’s thriving arts and entertainment scene is on display through plein air painting, block parties, live music, performing arts and gallery exhibits during the Third Annual Arts Week & Paint Annapolis June 1-9. http://annapolisartsweek.com

Bring your chair or blanket and settle in for an evening of fun at the Annapolis Towne Centre at Parole Friday Night Concerts. June 7 and every Friday through August 23.https://www.visitatc.com/events/friday-night-concert-series

Check your shoes at the optional “shoe dock” and enjoy an evening of cool drinks, groovin’ live music, tasty food, and to-die-for raffle items on the beach during the 14th Annual Bands in the Sand. June 8. www.cbf.org/bandsinthesand

Enjoy ten weeks popular local music – from rock, to folk, to jazz – against the backdrop of the incomparable Chesapeake during the 15th Annual Tides & Tunes Summer Concert Series. Thursdays, June 13 through August 15. https://amaritime.org/tides-tunes-summer-concerts-series

An estimated 35 bands are expected to perform on four stages – keeping local, original music front and center. Up and coming local bands representing a wide range of styles will display their talents alongside longtime favorites during Eastport a Rockin’. Tentative Date: June 22. www.eastportarockin.com

First Sunday Arts Festival, June 2 and every first Sunday of the month through November 3. www.firstsundayarts.com

Wednesday Night Sailboat Races. June 5, 12, 19, 26 through August 28. www.annapolisyc.com

Dinner Under the Stars. June 5, 12, 19, 26 and every Wednesday through September 18. www.dinnerunderthestars.org

July

Enjoy an old-fashioned community parade followed by fireworks over the Annapolis Harbor during the Annapolis Fourth of July Parade and Fireworks celebration. July 4. www.annapolis.gov

Many local bands perform at Nextival, and last year some up-and-coming musicians from New York, Washington, DC and Boston headed to the Crownsville fairgrounds to join the lineup. Tentative date: July 13. https://nextival.com

First Sunday Arts Festival, July 7 and every first Sunday of the month through November 3. www.firstsundayarts.com

Wednesday Night Sailboat Races. July 3 through August 28. www.annapolisyc.com

Dinner Under the Stars. July 3, 10, 17, 24, 31 and every Wednesday through September 18. www.dinnerunderthestars.org

Tides & Tunes Summer Concert Series. Thursdays, July 4, 11, 18, 25 through August 15. https://amaritime.org/tides-tunes-summer-concerts-series

Annapolis Towne Centre at Parole Friday Night Concerts. July 5, 12, 19, 26 and every Friday through August 23. https://www.visitatc.com/events/friday-night-concert-series

Quiet Waters Park Summer Concerts. July 6, 13, 20, 27 and every Saturday through August 24. http://fqwp.org

August

Enjoy ten weeks of popular local music – from rock, to folk, to jazz – against the backdrop of the incomparable Chesapeake during the 15th Annual Tides & Tunes Summer Concert Series. August 1, 8, 15. https://amaritime.org/tides-tunes-summer-concerts-series

74th Annual World’s Largest Crab Feast is an all-you-can-eat-and-drink tradition where more than 2,000 crustacean lovers typically finish off more than 300 bushels of freshly steamed #1 crabs (that's nearly 40,000 of the big ones!), 3,400 ears of corn, 100 gallons of crab soup, pit-beef, watermelon and hundreds of gallons of beer and soft drinks. August 2. www.annapolisrotary.org

The 29th Annual Annapolis Art Walk invites art lovers to indulge in a festive evening celebrating the arts. Eighteen galleries in downtown historic Annapolis are expected to host new art exhibits and feature artists demonstrating their skills in various media. August 15. http://www.artinannapolis.com/news.html

The 8th Annual Kegs and Corks Craft Beer & Maryland Wine Festival features unlimited samples of craft beer and Maryland wine, delicious food, awesome live bands – including AMISH OUTLAWS – and a variety of arts/crafts vendors. August 17.  www.kegsandcorksfest.com

Runner’s World Magazine calls it one of the top ten 10-mile races in the nation. Now in its 44th year, the Annapolis 10-Mile Run is conducted according to the road racing guidelines of the Road Runners Club of America. August 25. https://www.annapolisstriders.org

Immerse yourself in the culture of a 16th-century English village, complete with King Henry VIII and his court, at the 43rdAnnual Maryland Renaissance Festival, the second largest in the nation. Saturdays, Sundays and Labor Day, August 24 through October 20, rain or shine. https://www.rennfest.com

First Sunday Arts Festival, August 4 and every first Sunday of the month through November 3. www.firstsundayarts.com

Wednesday Night Sailboat Races. August 7, 14, 21, 28  www.annapolisyc.com

Dinner Under the Stars. August 7, 14, 21, 28 and every Wednesday through September 18 www.dinnerunderthestars.org

Tides & Tunes Summer Concert Series. Thursdays, August 1, 8, 15  https://amaritime.org/tides-tunes-summer-concerts-series

Annapolis Towne Centre at Parole Friday Night Concerts. August 2, 9, 16, 23, 30 https://www.visitatc.com/events/friday-night-concert-series

Quiet Waters Park Summer Concerts. Saturdays, August 3, 10, 17, 24  http://fqwp.org

September

 Immerse yourself in the culture of a 16th-century English village, complete with King Henry VIII and his court, at the 43rdAnnual Maryland Renaissance Festival, the second largest in the nation.Saturdays, Sundays and Labor Day, September 1 through October 20, rain or shine. https://www.rennfest.com

Enjoy seafood, interactive cooking demonstrations by the area’s best chefs, our famous crab soup cook-off, competitions, kids’ rides and activities, live entertainment and more at the 52nd Annual Maryland Seafood Festival. September 7-8. www.mdseafoodfestival.com

The 67th Annual Anne Arundel County Fair beckons visitors of all ages with fun contests, including hog calling and watermelon eating! Booths feature everything from homemade wine and home-brewed beer, to furniture and one-of-a-kind Christmas decorations. Kids will enjoy the amusement rides, 4H Club animals and more. September 11-15. www.aacountyfair.org

The 30th Annual Kunta Kinte Heritage Festival celebrates the perseverance, education and cultural heritage of people of African descent, commemorating the legacy of Kunta Kinte from Alex Haley’s Roots. It features live music and interactive dance performances on two stages and 80+ vendors. September 28. www.kuntakinte.org

Maryland Renaissance Festival, Saturdays, Sundays and Labor Day, September 1 through October 20, rain or shine. https://www.rennfest.com

First Sunday Arts Festival, September 1 and every first Sunday of the month through November 3. www.firstsundayarts.com

Dinner Under the Stars. September 4, 11, 18  www.dinnerunderthestars.org

October

The 48th Annual U.S. Powerboat Show is the nation’s oldest and largest in-water powerboat exhibition. It features more than 600 boats – everything from luxurious motor and ocean-going yachts and “down east” trawlers to high-performance boats and offshore fishing machines. October 3-6. http://www.annapolisboatshows.com/united-states-powerboat-show

Immerse yourself in the culture of a 16th-century English village, complete with King Henry VIII and his court, at the 43rdAnnual Maryland Renaissance Festival, the second largest in the nation. October 5-6, 12-13 and 19-20,rain or shine. https://www.rennfest.com

6th Annual Lifeline 100 Bicycle Event offers a unique organized ride experience for cyclists of all ages and abilities with scenic 100-, 65-, 30- and 15-mile route options as well as a free Children’s Bike Rodeo and Family Fun Ride. October 6. www.lifeline100.com

The 50th Annual U.S. Sailboat Show is recognized worldwide as the premier sailing showcase for seminars, boating attire and accessories, foul weather gear and boats of all sizes. Includes Cruisers University, a curriculum on cruising and boat preparedness; Brokerage Cove, featuring pre-owned brokerage sailboats; Vacation Basin, dedicated to chartering, travel, vacations and charter boat ownership; and more.October 10-14. http://www.annapolisboatshows.com/united-states-sailboat-show/

Enjoy food, live music by local artists, unique crafts, face painting and demonstrations showing the vital role oysters play in maintaining the health of the Chesapeake Bay at the 22nd Annual Captain Avery Oyster Festival. October 20. http://www.captainaverymuseum.org/

The Maryland Avenue and State Circle Fall Festival – Halloween on the Avenue is afamily-friendly event that includes musical entertainment, great shopping and – of course – tricks and treats! Tentative Date: October 20.https://www.shopmarylandavenue.com/

Maryland Renaissance Festival, Saturdays, Sundays October 5 through October 20, rain or shine. https://www.rennfest.com

First Sunday Arts Festival, October 6 and every first Sunday of the month through November 3. www.firstsundayarts.com

November

Drawing on a decades-old rivalry, the 22nd Annual Maritime Republic of Eastport Tug o’ War pits downtown Annapolitans against rebels of the mock-breakaway Maritime Republic of Eastport. Dubbed the “Slaughter across the Water,” it features the longest tug-of-war rope (1700 feet) over a body of water in the world and 450 tuggers in a series of heats. November 2.    http://themre.org

Annapolis by Candlelight showcases privately-owned historic houses. Visitors see how 21st-century Annapolitans care for, and live in, buildings constructed in the 18th, 19th and 20th centuries. Each house is a reminder of the architectural and cultural heritage of Maryland’s capital city. November 8-9. www.annapolis.org

Lights on the Bay is a spectacular drive-through holiday lights show beside the Chesapeake Bay. It features more than 70 animated and stationary displays, including traditional Maryland-themed favorites, holiday and children’s displays. November 23-January 1. http://www.lightsonthebay.org

First Sunday Arts Festival, November 3 and every first Sunday of the month through November 3. www.firstsundayarts.com

December

Are you a chocoholic in need of a fix? Don’t miss the 5th Annual Chocolate Binge Festival! More than 40 local chocolate vendors will be selling chocolate specialties, including chocolate bars, cakes, bars, caramels, truffles, fudge, cookies, candies, hot chocolate and more. Enjoy live music, roasting s'mores, a moon bounce, holiday market and a visit from Santa. December 1. www.annapolischocolatefestival.com

With support from the Annapolis business community, the Annapolis Jaycees (Junior Chamber of Commerce) host the Lighting of the Tree in Annapolis during the City’s Grand Illumination. Watch Santa arrive in town and enjoy singing and dance performances by area youth, Tentative date: December 1. https://www.annapolisjaycees.org

Lights on the Bay is a spectacular drive-through holiday lights show beside the Chesapeake Bay. It features more than 70 animated and stationary displays, including traditional Maryland-themed favorites, holiday and children’s displays. December 1-January 1. http://www.lightsonthebay.org

Lights, garland, action! Historic Annapolis shops throw open their doors in a glorified block party that’s open to all during Midnight Madness Holiday Shopping. Enjoy outdoor musical performances as well as food and refreshments at many stores along  Main Street, Maryland Avenue, West Street, State Circle and City Dock. December 5, 12, 19. www.downtownannapolispartnership.org/midnight-madness

More than 30 brightly lit boats bedecked for the holiday season parade around the Annapolis waterfront and Spa Creek during the 37th Annual Eastport Yacht Club Lights Parade. Thousands of lights and a host of jolly revelers make this a fun Christmas event for the entire family. December 14. www.eastportyc.org/lights-parade

The 12th Annual Military Bowl presented by Northrop Grumman, benefitting the USO of Metropolitan Washington-Baltimore (USO-Metro), will match a team from the Atlantic Coast Conference (ACC) against an opponent from the American Athletic Conference (AAC). Date to be announced. https://militarybowl.org

Family activities fill the day and music and dancing fill the night at the annual City of Annapolis New Year’s Eve Celebration. Children’s activities take place on Weems Whelan fields behind Maryland Hall and Bates Middle School. Afternoon festivities wrap up with on-site fireworks at approximately 5:15 p.m. The second round of festivities includes live music and dancing at City Dock, ending with midnight fireworks. December 31. www.annapolis.gov

About Visit Annapolis & Anne Arundel County:

Visit Annapolis and Anne Arundel County (VAAAC) is a nonprofit, membership-based Destination Marketing Organization (DMO) that generates revenues for the local economy by promoting Annapolis and the Chesapeake Bay to leisure and business travelers across the country and around the world. www.visitannapolis.org

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