Much of the Chesapeake Bay is pretty well-trodden on the tourist trail, but that doesn’t mean it is without merit. You don’t have to look far to find options beyond the T-shirt shops and soggy fries. Paddling and other water-based adventures abound around the bay, and a day on the water is best followed by sampling the offerings at one of the many breweries throughout the area. An Annapolis sailing charter is the ideal start to a classic summer vacation, so book it quick, grab some friends and head to the marina.
From Annapolis, you’ll head across the bay and south to the town of Cambridge on the Choptank River. Cambridge is lovely and historic and all, but strike out on a bike or a kayak or yacht charter to explore the coastal waters and forests. You have a couple of options for rentals in town. On the Rivet Bikes and Yaks rents beach cruiser–type bikes by the day or week. Blackwater Paddle and Pedal Adventures rent kayaks and bikes more suitable for longer journeys.
The public marina in Cambridge offers plenty of slips and good services, so you could comfortably spend a few days here exploring some of the 1,700 miles of river shoreline.
To get the most out of a paddle or ride anywhere around the Chesapeake, look up the Midshore Riverkeeper Conservancy. Part of the international network of Waterkeeper programs, MRC fiercely keeps watch over the Choptank and Wye Rivers and has contributed mightily to the cleanup and continued restoration of the local waterways. They offer paddling tours of creeks and watersheds and have the best recommendations for extensive bike routes. MRC also does agricultural outreach to help prevent fertilizer runoff, helping to preserve flora and fauna throughout the Chesapeake system.
Working up an appetite during the day, you can satisfy it at night by heading to RaR Brewing. The food gets lots of thumbs-up but more important is that the Beer Advocate website rates almost every brew from RaR quite highly. Ales, stouts, and lagers? Yes, yes, and yes. RaR, since opening in 2013, has become quite popular with visitors and locals alike, so snag a table early. From their basic Nanticoke Nectar to the Bucktown Brown to the Habanero Nectar, this place might be a reason to stay in Cambridge an extra night or two.
Points inland, east and west
Not really a lot of points, but the important ones, ie where the beer is. South and east about 36 miles from Cambridge is the town of Salisbury, Maryland, where you should schedule a visit at Evolution Craft Brewing Company, where the beer is delicious and the food created to match its bite for a drink. It’s the perfect stop-off point between the bay and the coast.
Of special note are the charcuterie and cheese selections and the housemade pickle samplers. The restaurant isn’t cheap, but on Wednesday and Sunday nights, they have specials that help bring your bill down. Among the lagers and ales, Evolution’s beer lineup includes the Rise Up Stout, which is brewed with coffee from the Rise Up roasting company located in nearby Easton.
Back on the western side of the bay and about an hour’s drive in from Annapolis, you’ll come to the burg of Frederick, Maryland. Although the town is more of a family-oriented destination, it does boast the well-established Flying Dog brewery, which is definitely worth the trip inland. Flying Dog has year-round, seasonal, and limited brews that draw people from miles around. The bottle artwork alone is worth your visit, but there’ll be plenty else to Chesapeake your interest.
Adventurous drinkers should order the Pearl Necklace Chesapeake Stout, which is brewed with oysters from the Rappahannock River. Proceeds from the sale of Pearl Necklace go toward helping restore the local oyster production. So order a few since it’s for a good cause and all. Summers at Flying Dog are especially fun, with the rooftop deck, happy hour events and games, silent disco, and more. Also, they fill growlers. Flying Dog is located at 4607 Wedgewood Boulevard.
Paddling adventures further afield
National Geographic Traveler rated neighboring Smith and Tangier Islands as must-see destinations for 2016. These sparsely inhabited islands are as much water as they are land, and kayaking through and around them is an incredible experience for those jonesing for a good, hard paddle. Both have been lauded and derided for their land-that-time-forgot qualities, but you’re not heading to Smith for the on-land sightseeing.
Smith is the northerly one and is accessible only by boat; a passenger ferry from Crisfield, the southernmost town in Maryland, which is also where you should rent your kayaks. Crisfield Kayak and Canoe Rentals can deliver boats around the area and get them over to Smith Island on the ferry for you. They will also provide you with plenty of information about water trails and what to see along the way.