An absolutely beautiful backdrop that includes the Chesapeake Bay, crown jewel of the Mid-Atlantic. Rolling countryside. A historic, seaport city dating back to Colonial times. A mega, state-of-the-art shopping and entertainment complex. All these and more lure visitors from around the globe.
Plus, every single month of the year, visitors to Annapolis & the Chesapeake Bay find a vibrant, dynamic community that boasts historical and maritime attractions, fun festivals and lively events. Here's what's happening in 2015:
Many resort towns shut down in January. Not Annapolis. The start of the General Assembly’s 90-day legislative session brings legislators, lobbyists, and advocates of various political causes to the center of historic Annapolis beginning in January. Each session opens with a sense of renewed vigor and purpose as politicians descend on the Maryland State House, the nation’s oldest in continuous legislative use (and also open year-round to tourists). As returning politicians flood the streets, restaurants and pubs of downtown Annapolis, their energy is contagious. Also, experience the positive energy at the Polar Bear Plunge, on January 24th, as brave participants take a frigid dip at Sandy Point State Park for a heart-warming cause: raising money for individuals with intellectual disabilities. Prefer something a little more low-key? Find a window seat at one of the area’s waterfront restaurants, enjoy a hearty meal or a drink with friends and, if you’re lucky, watch the January snow falling softly on the water.
Find a complete listing of January events in Annapolis & the Chesapeake Bay here.
Looking for a romantic getaway to celebrate Valentine’s Day? Consider Annapolis, voted one of America's Most Romantic Towns by TravelandLeisure.com. This quaint historic seaport town, with its brick-lined streets, colonial-era buildings, and cozy restaurants, deserves the title. On Sunday afternoons throughout February, if you’re situated at a window seat of a waterfront restaurant (or find yourself walking over the scenic Eastport Drawbridge), you might catch a glimpse of a unique Annapolis wintertime tradition: Frostbite Racing—wintertime sailing for the hardiest of sailors. Also, Annapolis Restaurant Week 2015 takes place February 24 – March 2, where dozens of to-die-for restaurants offer reduced rates on dining fare. Make a weekend of it when you spend the night in one of our quaint bed & breakfasts or modern, luxurious hotels.
Find a complete list of February events in Annapolis & the Chesapeake Bay here.
Historical and cultural happenings abound in March. On the weekend of March 20th, throughout Annapolis and Northern and Southern Anne Arundel County, Maryland Day commemorates the formal founding of the colony of Maryland. Historical, cultural and natural sites open their doors to the public with special tours, events, and programming for $1.00 or less. To commemorate “sock burning”, a quirky maritime rite of spring in which sailors burn their socks as a symbol of discarding the cold of winter, the Annapolis Maritime Museum on March 21, 2015 hosts its own lively Sock Burning and Oyster Roast. You needn’t be a sailor to join in the fun. On the heels of that exciting weekend, the Annapolis Film Festival returns for its third year in a row on March 26- 29. More than 70 films in four days, premiers, panel discussions, Q&A’s with filmmakers, and more promise to make this a must-do event.
Find a complete list of April events in Annapolis & the Chesapeake Bay here.
In April, everyone in the Annapolis & the Chesapeake Bay region is eager to get out and enjoy the warming weather. Two consecutive boat shows, the Bay Bridge Boat Show (April 17 – 19) and the Spring Sailboat Show (April 24-26), jumpstart the spring sailing season for both novices and veteran sailors alike. If you’re planning a visit to Annapolis in April, consider attending what’s become a beloved tradition: the St. John’s College vs. United States Naval Academy Croquet Match. In what’s likely the largest and most well-attended croquet match in the country, the Johnnies (students from St. John’s) and the Mids (Naval Academy midshipmen) compete each spring for the coveted Annapolis Cup. The festive atmosphere makes for a fun time for players and spectators alike.
Find a complete list of April events in Annapolis & the Chesapeake Bay here.
In Annapolis, the month of May begins with a truly beautiful tradition: May Day. On May 1, the doors of residences and businesses are adorned with baskets bursting with fresh-cut flower arrangements. Visitors roam the town oohing and aahing, and awards are distributed by judges from the Garden Club of Old Annapolis Towne to the decorated doors deemed most attractive. The baskets remain on display the first week of May. Another sight to behold occurs every Wednesday evening in May and throughout the summer season: Wednesday Night Sailboat Races. Whether you’re on deck or on the docks watching, a good time is had by all. For many, the most exciting time in May is Naval Academy Commissioning Week, a week-long celebration that includes a grand parade, a fly-over by the Blue Angels and more, culminating with a graduation ceremony for this year’s senior midshipmen.
Find a complete list of May events in Annapolis & the Chesapeake Bay here.
Fun, outdoor festivals and events dominate the entertainment landscape in June. The First Sunday Arts Festival, in downtown Annapolis every first Sunday May through October, is in full swing. This free street festival-slash-art market-slash-entertainment venue is not to be missed. Another fun arts festival in June? Paint Annapolis, a five-day juried plein air painting competition (June 8-14) in which artists from across the country descend on Annapolis, set up their easels outdoors, and allow passersby to look over their shoulders while they work (there’s also a competition component at the end of the festival). In keeping with June’s festive nature, there’s Eastport-a-Rockin’ (June 20), featuring a day of home-grown local music in a relaxed atmosphere on Eastport’s Back Creek.
Find a complete list of June events in Annapolis & the Chesapeake Bay here.
Warm summer weather brings more spectacular outdoor events in July. Everyone’s Irish for the weekend (July 10-11) at The Annapolis Irish Festival, where over 70 vendors and loads of live music bring a bit of the Emerald Isle to Annapolis. Live outdoor music reverberates throughout the region in July, as three concert series fill the air throughout the month: the Annapolis Maritime Museum Concert Series, Friday Night Concerts at Annapolis Towne Centre, and the Quiet Waters Park Summer Concert Series.
Find a complete list of July events in Annapolis & the Chesapeake Bay here.
When the sun is blazing and the pavement’s hot, loads of people in the Annapolis & Chesapeake Bay region take to the water: by sailboat, pleasure cruiser, kayak, paddle board—you name it. Both tourists and locals can be found in abundance on the water in August. For those who like to keep their feet on the ground, there is lots of fun traipsing about to be had—in the historic city of Annapolis, in the maritime villages of the Annapolis Countryside, or in the entertainment-shopping mecca in the Annapolis-Baltimore region. There's also the tasty Rotary Club Crab Feast held each year for those seeking a true taste of the Chesapeake.
Find a complete list of August events in Annapolis & the Chesapeake Bay here.
In September, the summer crowds disperse, the sun’s intensity wanes, and it’s a fantastic time to visit Annapolis and the Chesapeake Bay region. Enjoy historical sites and museums, crowd-free shopping and dining, and outdoor activities—whether hiking a trail at one of the area’s parks or paddling on the water. Also, consider taking in the Maryland Renaissance Festival in Crownsville. With this 22-acre fictional 16-century English village with over 200 performers, ten stages, a 5,000-seat jousting arena, 148 craft shops and 48 food/beverage facilities, it’s Maryland's premier outdoor event.
Find a complete list of September events in Annapolis & the Chesapeake Bay here.
What comes to mind when you think of October—fall foliage, football, and Halloween, right? Well, you’ll find it all here. In the beautiful Annapolis countryside, family-friendly fall festivals abound. Think hayrides, big fat pumpkins, corn mazes, and all the things that make this time of year memorable for kids. For grown-up kids or youngsters who can handle a spine-tingling thrill, check out Annapolis’ haunted tours. You’ll be spooked by centuries-old tales of Annapolis’ long-deceased inhabitants. When it comes to fun fall traditions, you can’t beat Navy Football. Join the crowd at the Navy-Marine Corps Memorial Stadium and embrace the tradition and excitement that permeates the stands. If you’re a sailor, boater, or just dreaming of getting on the water, come to our fall Boat Shows. On consecutive weekends, the U.S. Sailboat Show (October 8 thru 12) and the U.S. Powerboat Show (October 15 thru 18) present two of the most extravagant, in-water boat shows in the nation.
Find a complete list of October events in Annapolis & the Chesapeake Bay here.
observe the biggest Tug of War over a body of water between decades’-old rivals Eastport and Annapolitans. Known as “Slaughter across the Water”, it’s become a beloved annual charitable event with a party on each side afterwards. Spectators can view the spectacle from City Dock on the Annapolis side or, on the Eastport side, Second Street near the Chart House Restaurant. For a spectacle of a different sort, pack the kids in the car and head to Sandy Point State Park any night beginning mid-November for Lights on the Bay, a spectacular drive-through holiday lights show beside the Chesapeake Bay featuring more than 60 animated and stationary displays. Another beautiful display happens just one evening in November: Annapolis by Candlelight. During this walking tour in historic Annapolis, participants glimpse the interior of some of the city’s most impressive historic private homes.
Find a complete list of November events in Annapolis & the Chesapeake Bay here.
Voted one of the best towns for the holidays by Travel & Leisure, Annapolis is a must-see in December. The downtown streets of Annapolis are all gussied up with garland and lights, and just a stroll around town is enough to get you into the holiday spirit. But there’s more. The Eastport Yacht Club Lights Parade, on the second Saturday of December at 6:00 p.m., draws a merry crowd to watch as 30-plus beautifully decorated boats light up the Annapolis Harbor. Midnight Madness, on two consecutive Thursday evenings in December, brings out shoppers and revelers as the stores in downtown Annapolis stay open until Midnight. The excitement doesn’t die down after Christmas. Football fans descend on the Navy-Marine Corps Memorial Stadium for an exciting college bowl game, the Military Bowl (date TBD). The city of Annapolis also holds a fun, family-friendly New Year’s Eve Celebration beginning at 3:00 p.m. on December 31st at City Dock and concluding with festive fireworks.
Find a complete list of December events in Annapolis & the Chesapeake Bay here.