February 3, 2023
Annapolis, US 30 F

Busy Weekend For Annapolis

As I look at the calendar, I see that this weekend (May 4-6) is a killer for things to do.  So, here’s the list that I have so far!  If you have something to add, please leave a comment.

Chesapeake Bay Wine Festival. Bay Bridge Marina, Stevensville. Saturday May 5th and Sunday May 6th. (noon to 6pm). Tickets $30, $60 (VIP), and $10 (Designated Driver). Available online.

Come by boat, plane or car to the 5th Annual Chesapeake Bay Wine Festival May 5 and 6, 2012. Join us as we kick off the season at the Bay Bridge Marina on beautiful Kent Island, MD. General Admission tickets include a commemorative wine sampling glass, samples of all wines featured by our twelve wineries, craft beer and microbrew tastings, sangria tastings (don’t forget to vote on your favorite!), and live entertainment provided by several local bands (more info on Entertainment page). VIP tickets include all of the above plus a private tent near the live music and a special catered reception by Hemingways Restaurant. This beautiful and scenic venue is the perfect place to spend your weekend, sipping local and international wine as well as carefully selected microbrews.

Naptown barBAYq. Anne Arundel County Fairgrounds. Friday, May 4th and Saturday May 5th. (4pm to 10pm Friday, 11am to 10pm Saturday). Tickets $5. Available online.

Competing BBQ teams will spend Friday and Saturday slicing, seasoning and sizzling pork, chicken and beef in hopes of winning some of the $9,000 in cash prizes along with all-important bragging rights on the Kansas City Barbeque Society (KCBS) BBQ Circuit. While the BBQ teams compete, your family will enjoy live music from 32 bands on two stages. Many different types of food and drink will be available including some cooked by the competing BBQ teams: pulled pork sandwiches, chicken, ribs and beef BBQ as well as other traditional BBQ fare plus delicious offerings from local food vendors.

Annapolis Comedy Festival. Rams Head On Stage. Saturday, May 5th (2pm-all ages, 7pm, 10pm). Tickets $10 for all ages, $20 for adults only. Available online.

The Annapolis Comedy Fest brings nationally-recognized, professional comedians to Annapolis for a celebration of improvisational comedy. The 2012 Annapolis Comedy Fest will be held on Saturday, May 5. There will be three shows – a 2:00 pm all ages matinee and two 20 and over shows at 7:00 pm and 10:00 pm. All events will take place at the Rams Head Tavern at 31 West Street in Annapolis, Maryland.

First Sunday Arts Festival. Calvert & West Streets.  Sunday, May 6th. FREE.

First Sunday Arts Festival is a Free Annapolis arts and craft show featuring about 100 local and regional artists. Plus be entertained with live music, dance, street performers, food and more. This event is on the first Sunday of each month May to October on Calvert and West Streets in Historic Annapolis, Maryland. Thousands attend, both locals and tourists buying from local and regional artists and crafters.

City Fair. City Dock at National Sailing Hall of Fame. Saturday, May 5th and Sunday May 6th (10am to 6pm Saturday, noon to 6pm Sunday). FREE.

Take part in a celebration of the City of Annapolis, as it showcases the services, opportunities and diversity of our historic community. This interactive weekend will include pony rides, a Lego building station, demonstrations of the Jaws of Life, and a life-sized chess game.

Annapolis Sperry Top-Sider NOOD Regatta. Annapolis Yacht Club. May 4th through May 6th. FREE to watch.

The Sperry Top-Sider NOOD Regattas will sail into nine cities, including Boston, Mass.; Chicago, Illinois; Houston, Texas; Larchmont, N.Y.; San Diego, Calif.; St. Petersburg, Fla.; Annapolis, Md.; and Toronto, Ontario, Canada. The overall winner at each location will receive a Sunsail charter during the Sperry Top-Sider NOOD Regatta Championship, in the British Virgin Islands, where they will compete against the overall winners from each stop on the nine-regatta Sperry Top-Sider NOOD circuit.

Cinco de Mayo Festival. West Annapolis. May 5th. FREE.

Celebrate with the folks in West Annapolis as they welcome in Cinco de Mayo. And if you want, partake in a special Cinco de Mayo Bar Tour with Barhopolis as they celebrate downtown with special pricing in several favorite watering holes. (Use the code EYEONCINCO to save 50%)

Chesapeake Bayhawks Lacrosse. Navy-Marine Corps Memorial Stadium. May 5th (7pm). Tickets $15, $20, $75. Available online.

Don’t forget about the Chesapeake Bayhawks home opener against the Ohio Machine on Saturday night. Come see Annapolis’ own Major League Lacrosse team play at Navy-Marine Corps Memorial Stadium.

Cinco de Mayo Cruise. City Dock. May 5th (8pm to 11pm). Tickets $28. Available online.

We are celebrating with a special “Cinco de Mayo Cruise” in Annapolis featuring Latin themed drinks, food and music. Latin tunes will be played as entertainment. Watermark’s signature margaritas and Coronas will be available for purchase. We will also have a special menu of Mexican and Hispanic foods for purchase on board. Both our vessel and our staff will be dressed up in Cinco de Mayo garb to add to the festivitives. B.Y.O.S. – Bring your own sombrero to this unique Cinco de Mayo event in Annapolis.

Camp Blaze 26th Annual Children’s Fair. Big Vanilla, Arnold, MD. May 5th (9am to 3pm). FREE.

The annual Children’s Fair is a central part of Camp Blaze’s mission. We believe the success of our children requires strong and connected families linked to a family-focused community including the workplace, churches, government, education, recreation and non-profit agencies. The Children’s Fair is an effective way to spotlight the community’s family-focused resource base.

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