A friend asked us to recommend locales in the middle Bay from which he and his wife could launch day and weekend trips. Here we’ve included our advice to him, plus a couple of Northern and Southern Bay gems to put on your summer list. We’ve skipped the big cities—Baltimore, Annapolis, Alexandria, VA, and Washington, DC—to stay focused on the towns that don’t get as much press. The Chesapeake Bay is vast, so keep in mind that this is just a sampling. We welcome your additions anytime; email them to [email protected].
Starting at the top
PropTalk readers remember our recent “See the Bay” articles about Chesapeake City and North East. Chesapeake City, which resides along the C&D Canal, boasts historic bed and breakfasts, waterfront restaurants, the C&D Canal Museum and Trail, and importantly for boaters, free docking at city dock, transient slips at the Chesapeake Inn and Schaefer’s Canal House, and a protected anchorage just beyond the Inn’s Tiki Bar.
If you turn back down the Elk River, turn right at the Turkey Point Lighthouse, and continue up the Bay, you reach North East. This town is so far up the Bay that recently when we visited a PropTalk customer, he said, “Welcome to Pennsylvania!” He was kidding, of course. Many boaters know the town for the Nauti-Goose Restaurant (read: ample docking and deck bars), and a 13-acre waterfront park beyond it, where they find the Upper Bay Museum. It’s a quaint Main Street, too, with Woody’s Crab House and a memorable chocolate shop, North East Chocolates, across the way.
We haven’t forgotten about that other town at the top, Havre de Grace (we have a “See the Bay” article about it coming in September). It may have burned to the ground during the War of 1812, but 200 years later, it was named one of America’s best small towns to visit by Smithsonian Magazine. A number of marinas welcome transient boaters to this very walkable town, including the four-mile Lafayette Trail that’s satisfying to history lovers and health buffs alike. Don’t forget the Maritime Museum along the trail. A First Friday Festival welcomes visitors May through October, which gives you a good excuse to start the weekend early.
The Shore with a capital “S”
Some folks think there’s no need to ever cross the Chesapeake Bay Bridge (or the Bridge-Tunnel) if you can stay on the Eastern Shore. One Shore destination to put on your list this season is Chestertown… and if you’re motivated, act quickly, because the Chestertown Tea Party and Festival unfolds May 27-29. One of the town’s biggest events, it includes live music, kids’ activities, schooner rides, and reenactments of Maryland’s own tea party that has nothing do to with politics anymore.
The 24-mile journey from the Bay to Chestertown is more important than the town itself for many boaters. The tree-lined Chester is long, winding, and filled with anchorages and creeks you could spend all summer exploring. Those who prefer quiet may never make it all the way to Chestertown!
Rock Hall. This watermen’s town does Fourth of July fireworks that can’t be beat. The Pirates and Wenches Fantasy Weekend (August 12-14) has become a huge hit. But even on an “ordinary” weekend in summer, a crab cake at Waterman’s Crab House and some live music on the deck are must-dos.
Thick in the middle
That’s a good thing. The mid-Chesapeake is teeming with weekend destinations. There’s a reason you see so many boaters roaring in and out of the South River, and it goes beyond Mike’s Crab House on the north side of Beard’s Creek (as good of an excuse as any to go up the river). There are many creeks to explore up this river. Harness Creek is a popular one on weekends, and visitors can expect to meet other boaters, kayakers, SUP enthusiasts, and swimmers along the shores of Annapolis’s Quiet Waters Park, so proceed with caution.
A popular destination up the West River is Galesville, one of the oldest villages in the United States. Boaters like it because it’s friendly and pretty and has good marinas for transients as well as two watering holes worth visiting: Pirate’s Cove and Thursday’s.
If you’re considering crossing the Bay to St. Michaels, as we recommend you do, read up on it at proptalk.com/see-the-bay-st-michaels.
If you steer out of the Eastern Bay and turn left to pass Poplar and Tilghman Islands, you then turn left to head up the Choptank to Cambridge. If you plan on visiting this quiet town, whether to the Hyatt Resort or one of the other nice marinas, know that it will be exceptionally loud and exciting Memorial Day weekend, as the Cambridge Classic powerboat racing event will take place. The Seafood Feast-i-val August 13 might be one to put on your list. If you go when there are no crowds or festivals, we recommend the High Spot Gastropub in High Street.
Y’all go south
When you start seeing pelicans, and you can taste the salt in the spray, you’ve reached the gateway to the southern part of the Bay at Solomons. The Calvert Marine Museum’s excellent exhibits and summer concert series are only two of the many reasons to visit. Great marinas, bike and small boat rentals, shops along a walkable, waterfront Main Street, good food, and a vacation vibe draw us back to this town at the mouth of the Patuxent River.
Now let’s leap past the Potomac (that’s a weeklong excursion in itself!) and visit Irvington, VA, 11 miles up the Rappahannock River in Carter’s Creek. We’ve never met a boater who regretted a weekend jaunt to the Tides Inn. Golf, spa, beachside pool, restaurants, bicycles for exploring by land, and 24 transient slips: what’s not to like? Learn more at proptalk.com/lancaster-county-va.
One more stop for this trip (like we said, there are many, many more)… let’s cross the Bay a bit farther south and visit Cape Charles, a reinvigorated town with great marinas and restaurants. If you enter into Cherrystone Channel into Kings Creek, proceed cautiously and pay attention to the channel and stay close to your red channel markers. At the Oyster Farm at King’s Creek for the Shuck-n-Suck, August 4-7, oyster buy boats return for their 12th annual reunion. This will kick off a brand new event featuring raw oysters, roasted oysters, fried oysters, and more from all over the Shore, such as a boat-docking contest, Smith Island Crab Skiff races, and live music.
What’s your favorite day trip or weekend excursion on the Chesapeake? Send it to [email protected].
Wednesday, June 1, 2016 - 08:45
A friend asked us to recommend locales in the middle Bay from which he and his wife could launch day and weekend trips. Here we’ve included our advice to him, plus a couple of Northern and Southern Bay gems to put on your summer list. We’ve skipped the big cities—Baltimore, Annapolis, Alexandria, VA, and Washington, DC—to stay focused on the towns that don’t get as much press. The Chesapeake Bay is vast, so keep in mind that this is just a sampling. We welcome your additions anytime; email them to [email protected].
Starting at the top
PropTalk readers remember our recent “See the Bay” articles about Chesapeake City and North East. Chesapeake City, which resides along the C&D Canal, boasts historic bed and breakfasts, waterfront restaurants, the C&D Canal Museum and Trail, and importantly for boaters, free docking at city dock, transient slips at the Chesapeake Inn and Schaefer’s Canal House, and a protected anchorage just beyond the Inn’s Tiki Bar.
If you turn back down the Elk River, turn right at the Turkey Point Lighthouse, and continue up the Bay, you reach North East. This town is so far up the Bay that recently when we visited a PropTalk customer, he said, “Welcome to Pennsylvania!” He was kidding, of course. Many boaters know the town for the Nauti-Goose Restaurant (read: ample docking and deck bars), and a 13-acre waterfront park beyond it, where they find the Upper Bay Museum. It’s a quaint Main Street, too, with Woody’s Crab House and a memorable chocolate shop, North East Chocolates, across the way.
We haven’t forgotten about that other town at the top, Havre de Grace (we have a “See the Bay” article about it coming in September). It may have burned to the ground during the War of 1812, but 200 years later, it was named one of America’s best small towns to visit by Smithsonian Magazine. A number of marinas welcome transient boaters to this very walkable town, including the four-mile Lafayette Trail that’s satisfying to history lovers and health buffs alike. Don’t forget the Maritime Museum along the trail. A First Friday Festival welcomes visitors May through October, which gives you a good excuse to start the weekend early.
The Shore with a capital “S”
Some folks think there’s no need to ever cross the Chesapeake Bay Bridge (or the Bridge-Tunnel) if you can stay on the Eastern Shore. One Shore destination to put on your list this season is Chestertown… and if you’re motivated, act quickly, because the Chestertown Tea Party and Festival unfolds May 27-29. One of the town’s biggest events, it includes live music, kids’ activities, schooner rides, and reenactments of Maryland’s own tea party that has nothing do to with politics anymore.
The 24-mile journey from the Bay to Chestertown is more important than the town itself for many boaters. The tree-lined Chester is long, winding, and filled with anchorages and creeks you could spend all summer exploring. Those who prefer quiet may never make it all the way to Chestertown!
Rock Hall. This watermen’s town does Fourth of July fireworks that can’t be beat. The Pirates and Wenches Fantasy Weekend (August 12-14) has become a huge hit. But even on an “ordinary” weekend in summer, a crab cake at Waterman’s Crab House and some live music on the deck are must-dos.
Thick in the middle
That’s a good thing. The mid-Chesapeake is teeming with weekend destinations. There’s a reason you see so many boaters roaring in and out of the South River, and it goes beyond Mike’s Crab House on the north side of Beard’s Creek (as good of an excuse as any to go up the river). There are many creeks to explore up this river. Harness Creek is a popular one on weekends, and visitors can expect to meet other boaters, kayakers, SUP enthusiasts, and swimmers along the shores of Annapolis’s Quiet Waters Park, so proceed with caution.
A popular destination up the West River is Galesville, one of the oldest villages in the United States. Boaters like it because it’s friendly and pretty and has good marinas for transients as well as two watering holes worth visiting: Pirate’s Cove and Thursday’s.
If you’re considering crossing the Bay to St. Michaels, as we recommend you do, read up on it at proptalk.com/see-the-bay-st-michaels.
If you steer out of the Eastern Bay and turn left to pass Poplar and Tilghman Islands, you then turn left to head up the Choptank to Cambridge. If you plan on visiting this quiet town, whether to the Hyatt Resort or one of the other nice marinas, know that it will be exceptionally loud and exciting Memorial Day weekend, as the Cambridge Classic powerboat racing event will take place. The Seafood Feast-i-val August 13 might be one to put on your list. If you go when there are no crowds or festivals, we recommend the High Spot Gastropub in High Street.
Y’all go south
When you start seeing pelicans, and you can taste the salt in the spray, you’ve reached the gateway to the southern part of the Bay at Solomons. The Calvert Marine Museum’s excellent exhibits and summer concert series are only two of the many reasons to visit. Great marinas, bike and small boat rentals, shops along a walkable, waterfront Main Street, good food, and a vacation vibe draw us back to this town at the mouth of the Patuxent River.
Now let’s leap past the Potomac (that’s a weeklong excursion in itself!) and visit Irvington, VA, 11 miles up the Rappahannock River in Carter’s Creek. We’ve never met a boater who regretted a weekend jaunt to the Tides Inn. Golf, spa, beachside pool, restaurants, bicycles for exploring by land, and 24 transient slips: what’s not to like? Learn more at proptalk.com/lancaster-county-va.
One more stop for this trip (like we said, there are many, many more)… let’s cross the Bay a bit farther south and visit Cape Charles, a reinvigorated town with great marinas and restaurants. If you enter into Cherrystone Channel into Kings Creek, proceed cautiously and pay attention to the channel and stay close to your red channel markers. At the Oyster Farm at King’s Creek for the Shuck-n-Suck, August 4-7, oyster buy boats return for their 12th annual reunion. This will kick off a brand new event featuring raw oysters, roasted oysters, fried oysters, and more from all over the Shore, such as a boat-docking contest, Smith Island Crab Skiff races, and live music.
What’s your favorite day trip or weekend excursion on the Chesapeake? Send it to [email protected].