Things to Do in Parole

At the Maryland Drafts and Laughs Festival, attendees sample suds from taps dispensing more than 50 craft and imported brews. As festival-goers make their way among breweries such as Port City and Yuengling, they can break for comic relief at one of five standup shows. There, regional comedians culled from Last Comic Standing, Comedy Central, and Sirius XM Radio entertain with adult-brand humor. Visitors can also sit in on presentations and Q&As with brew masters from Flying Dog and Heavy Seas, asking them about their unique brewing process or how many elves it takes to seal a beer can once it's been filled. To sustain the unlimited sampling, food and soda will be available for purchase.

When Pete and Kate Vonderheide moved from Hawaii to Annapolis to live closer to their family, they thought they'd have to give up a career of ocean kayaking to resume responsible office jobs. Soon they recognized the historic city harbor's lack of kayak tours and knew they couldn't stay inside forever. Their shared passion for history spurred them to research and interview the locals until they'd compiled enough historic material to start leading tours. Today, their tours can teach something new even to locals.

The Vonderheides continue to assemble a team of outdoor guides certified in CPR and first aid who all bear a well-researched knowledge of area wildlife and history. These experts lead two-hour scenic tours through the historic harbor. Starting each excursion with a brief paddling lesson, they put first-timers at ease with basic instruction and an amiable demeanor, unlike guides who rely only on their convincing Captain Ahab impressions. Excursions begin at the Spa Creek headwaters in Truxtun Park and lead participants into open-harbor waters to drift in full view of the state capitol building, the US Naval Academy, and historic Eastport. Trips peak at the City Dock, where participants receive a break to take photos and rest. On the return trip, guides field open-ended questions about city history such as presidential visits, the crabbing and oystering trade, and whether George Washington had to swim using floaties.

Since its first event in 2008, the Chesapeake Bay Wine Festival has steadily added to its multisensory feast of libations, food, and live sounds. Originally conceived to highlight Maryland's wines, beers, and local delicacies, the festival now brings wines from around the world to its bayside location. White tents shield tasters from rain, sunburn, and any curious fish who might try to leap into their goblets. Each year, the festival benefits an array of community- and family-focused organizations.

Chesapeake Bay is 200 miles long, but that’s not the only reason it’s the United States’ largest estuary. The Bay also serpentines off into hundreds of rivers and creeks, accessible with South River Boat Rentals’ vessels. Seafarers explore the estuary’s fringes in the powerboats and sailboats, cruising past historic sites, such as Jamestown and Tangier Island. Alternatively, fishing parties set sail for piscatorial hot spots, casting from the boats’ decks. To teach newbies the ropes before they hit the water, the company’s team hosts sessions on boating basics, from steering to stopping at fish crossings.

In October, representatives from regional, local, and national craft breweries gather inside the Navy-Marine Corps Memorial Stadium to pour samples of geek-lovers brews. Visitors sip on signature standards from breweries such as Oskar Blues, Union Craft Brewing, Old Dominion, Starr Hill, Heavy Seas, and Flying Dog Brewery, along with special varieties of bourbon-barrel-aged stouts, whiskey-barrel-aged ciders, and hearty IPAs.

When not enjoying beer-related activities, festival-goers can check out one of the eight live bands playing all afternoon on two stages or take in the display of antique and exotic cars. The stadium catering company serves local delicacies such as Maryland crab cakes, shucked oysters on the half shell, and crab-and-cheese pretzels. More than 60 merchandise vendors offer artisan crafts and specialty food items.

For the last two years, runners from across Maryland have gathered for the Be Great 5K Run & Fun Walk to benefit the Annapolis Boys & Girls Scholarship Trust. The trust has provided financial support to more than 25 students to help them attend college over the last 10 years, and proceeds from the race go toward the scholarship fund. Before the race, runners are given a bib that tracks their time and pace better than an hourglass taped to their torso. After crossing the finish line, racers are rewarded with refreshments, and a lucky few are awarded prizes.