We at PropTalk love to show off our home port of Annapolis to out-of-town boating friends. Whether you have traveled from as close as Baltimore or as far as California, we welcome you to Maryland’s capital city! With PropTalk staffer favorites mixed in, here are 10 recommendations for things to do outside the Annapolis Powerboat Show gates in 2024, starting with drinks and food followed by activities.
1. What’s new?
As we went to print, the Timber Pizza Company was opening its brand-new location at 192 West Street. The wood-fired pizza chain has been popular in Virginia and Washington, DC, so we’re excited to have a new local hangout. Two doors down (196 West Street), you will find the Sailor Oyster Bar. We were sad when this cool oyster bar burned down a couple of years ago—it’s back! A great spot to have some smoked white fish dip and a cocktail.
2. What’s brewing?
The long-awaited Chessie’s Wharf, the Annapolis location of RaR Brewery (“local boys brewing local beers” in Cambridge, MD) is open in West Annapolis, offering 38 brew selections and yummy food. A PropTalk staffer favorite, Forward Brewing (418 Fourth Street, Eastport), will celebrate Oktoberfest October 4-5 with Forward’s 2024 glass, pints of Oktoberfest (Marzen-style lager), house-made pretzels, sausage pretzels, and good cheer… Prost!
3. Wine and dine.
What to do if your date doesn’t drink beer? Break up! Kidding. We have solutions: Locals like Vin 909 Winecafé (909 Bay Ridge Avenue). Parking is not always easy; getting a table is not always easy; you might wait in line; but you’ll love the farm-to-table food and excellent wines as we all do. If you’re in town for more of a Main Street Annapolis vibe, check out Red, Red Wine Bar. They have wines on tap and decent food.
4. Meet you at the pub!
Come as you are to any of Annapolis’s great pubs: Davis’ Pub (400 Chester Avenue), “where there are no strangers; only friends you’ haven’t met yet,” is as local as pubs get. The Boatyard Bar & Grill (400 Fourth Street), another PropTalk favorite, has an extensive menu and raw bar (and kids’ menu and coloring books). Closer to the boat show, yet far enough away to find a seat, Galway Bay Irish Pub (63 Maryland Avenue) boasts a nice selection of beers (Guinness!), excellent food, and a friendly staff. The Ram’s Head Tavern (33 West Street) is a reliable staple, as is Reynold’s Tavern and 1747 Pub (7 Church Circle)—sit out back on a nice day or down in the cozy basement by the fireplace when it’s chilly.
5. Follow the ice cream trail.
Boat show regulars know that it can feel 10 or 15 degrees warmer inside the show gates, especially on a busy sunny day. If you need some ice cream to cool off, follow the trail: Storm Bros. Ice Cream is on the same block as the Boat Show Main Gate and an easy one… unless there’s a line. You may have to walk to stop #2 on the trail: Kilwins Chocolate and Ice Cream Shop at the foot of Main Street (try the Blueberry Waffle Cone or Annapolis Mud flavors).
Kilwins too busy? Keep walking uphill until you find the Annapolis Ice Cream Company and all kinds of homemade goodness. Too busy? Walk a few doors uphill to find Proptalk staffer Beatrice’s favorite: the Red Bean. Beatrice says, “Hands down, best ice cream I’ve ever had. They use milk from a local dairy farm to make their own ice cream and mix your custom flavor ready to order—and the seasonal pumpkin flavor should be coming back soon!”
6. Hop onboard.
If you are itching to see Annapolis by boat, a quick and easy option is to find a Water Taxi at the waterfront stop between the Annapolis Waterfront Hotel and Eastport Bridge. You can also call (410) 263-0033 or hail “water taxi” on VHF radio channel 68. Two other options to consider: Darling Charters for custom day charters on a pretty picnic boat and Annapolis Electric Boat Rentals for a turn-key electric boat, “like a Tesla, but slower,” for exploring Annapolis creeks.
7. Visit “The Yard” at the U.S. Naval Academy
If you’ve never visited the U.S. Naval Academy (USNA), it’s worth a few hours of your time! For starters, enter the Armel-Leftwich Visitor Center to watch the moving 13-minute film, “The Call to Serve,” which repeats every 15 minutes.
The exhibit area is a mini-museum with several interactive screens, including maps and guidance to help you orient yourself on the Yard. There are several kiosks with interactive videos featuring midshipmen and recent graduates who discuss admissions, academics, student life, and career options. With more than 700 photographs and heart-stopping photography of the U.S. Naval Academy’s most iconic moments, you’ll feel the spirit right from the start. Check out the USNA gift shop and the museum, because you will need your own “Go Navy!” tee shirt.
Want to get the best view of what life is like on the Yard? Join an historical tour. Professional guides from the Naval Academy Business Services Division lead you through the places that have trained the best and the brightest and brought this leadership school of approximately 4400 wayfinders to vibrant life. The USNA provides a number of guided tour options.
When you’re exploring the Yard, you’re also giving back in a meaningful way, since 100 percent of the profits from tours, merchandise, and meals purchased go to support the Brigade of Midshipmen. The Visitor Center is open daily from 9 a.m. to 5 p.m. as is the USNA Gift Shop. Learn more and buy tickets at navalacademytourism.com/visitor-center.
8. Annapolis Highlights: A Walking Tour
Did you know that the Kunta Kinte character in the famous television series “Roots” was based on a real African boy who entered the United Staes through the port of Annapolis? Or that 24 percent of the U.S. Navy officers resigned to fight with Confederate forces during the Civil War? Discover these stories and more on the self-guided audio tour “Annapolis Highlights: Sailing Through History” on the TravelStorys mobile app.
As you approach significant landmarks around downtown Annapolis, this walking tour’s audio triggers automatically. The narration is accompanied by an interactive map and a virtual exhibit hall of images, text, and weblinks. Simply download the TravelStorys app to your phone, select and download the tour, and hit play!
This audio tour is presented in partnership with the EWE Spirit Foundation, a nonprofit organization dedicated to honoring the legacy of local sailor Geoff Ewenson by helping those facing immediate hardship bridge financial and social support gaps through mentorship, outreach, and financial assistance (ewespirit.org).
9. Dragonfest
Come to Pier 4 Marina in Eastport on Sunday, October 13, to kick off Breast Cancer Awareness Month with the third annual Dragonfest. Everyone who wears Annapolis Dragon Boat Club gear will receive a free raffle ticket. Entry is free.
The festivities include live music by Rickshaw Lizard plus a raffle, 50/50, silent auction, and wine pull. Special fun activities for the kids. The menu includes BBQ, oysters, hot dogs, keg beer, water, and sodas.
The Annapolis Dragon Boat Club is a 501(c)(3) nonprofit, all-volunteer organization that offers exercise and camaraderie to those in our community diagnosed with breast cancer. Paddling on the beautiful Spa Creek heals participants’ minds and bodies. Proceeds will go directly to furthering the organization’s mission of improving the lives of breast cancer survivors and their families and friends: annapolisdragonboatclub.org.
10. Raise the Woof!
PropTalk readers love their boat dogs! Join Peake Social for the second Barktoberfest for steins and canines as they celebrate German-style beer, Bavarian food, and pawesome four-legged friends October 5 at Annapolis Town Center.
Returning is the crowd favorite dog fashion/costume show, imported and locally crafted brews, and yard games. A portion of the proceeds will go directly to the Anne Arundel SPCA. Dogs that are friendly and on a leash are welcome but should be comfortable with crowds and other dogs nearby.
The event will go on rain or shine and is free to the public, but you do need a ticket. Register on the Annapolis Town Center webiste. While supplies last, each person who adopts a dog will receive a free canine PFD. We spoke with a volunteer instructor with the Maryland Department of Natural Resources (DNR) who shared that the goal of the event is to “adopt and protect.”