While generally there are no specific geographic boundaries for the portion of the Chesapeake many folks call the “Middle Bay,” most people consider the expanses of water south of the Bay Bridge and north of the Patuxent River part of that region. And a beautiful region it is. But first you’ll have to wrangle four days off from your boss, and that may be the biggest challenge of your trip.
Start the five-day cruise in Annapolis, which is convenient from many parts of the Bay, and then travel south to Galesville, MD, off the West River. On the third day, hop across the Chesapeake into Eastern Bay to St. Michaels, then head back out into the Bay and jog through Knapps Narrows. From there, head up the Choptank River to the visually pleasing Tred Avon River and Oxford, MD. If you’re cruising to the Middle Bay from the south, you can reverse the order and start out in Oxford.
Day One: Annapolis (NOAA Chart 12282)
Annapolis-proper is situated on Back and Spa creeks off the Severn River about six miles southwest of the Bay Bridge. While Annapolis’ ZIP codes encompass many more bodies of water, we’ll focus on the downtown and Eastport sections of town, which is where most of the activity happens. Navigationally speaking, flashing red bell buoy “2” is a good entrance mark to shoot for from the main Bay stem (especially if you approach from the south), but you also can shoot for flashing red “4” off Tolly Point a bit farther north and west of flashing red bell buoy “2.”
Keep an eye out for the thousands of crab trap floats that pepper the water as you approach. If you’re bound for Eastport and Back Creek, head for flashing green “1E” from Tolly Point. If bound for downtown Annapolis, follow the river marks in, making sure you give flashing white “HP” at Horn Point a wide berth before turning west toward the harbor.
Annapolis leads a double-life. While the downtown area is accented by City Dock, the U.S. Naval Academy, the State House, and the Historic District, Eastport, located just south, is the maritime-centric hub. The city of Annapolis manages a number of moorings on both Spa and Back creeks, which are first-come, first-served. Simply pick up one of the heavy-duty mooring pennants and the harbormaster will come by boat to collect the $25-$30 fee. The water taxi (410-263-0033 or on VHF Channel 68) runs around Spa and Back creeks for the basic fee of $2 (higher for longer trips). If you’re interested in getting away from it all, you’ll generally need to head up the Severn River, which has quiet creeks for exploration and anchoring.
Slip space at marinas is almost always at a premium in Annapolis, so you will want to secure a reservation before your trip commences. That said, marinas are everywhere and range from small operations to large, full-service spots that can take megayachts.
Ashore are too many attractions, restaurants, bars, and tours to list here, but you can certainly make a day or evening of it by just having the water taxi drop you off at City Dock. You’ll easily find your way to ice cream, dinner, lunch, drinks, shopping, or just about anything else. A visitor information center at City Dock next to the Harbormaster’s office is open daily March through October from 9 a.m. until 5 p.m. Eastport is just across Spa Creek and a great place to grab a nice bite to eat. PropTalk likes Boatyard Bar & Grill, Leeward Market, and Davis’ Pub, for starters.
Day Two: Galesville (NOAA Chart 12270)
Leaving Annapolis, head out the Severn River and turn south at Tolly Point (flashing green “1AH), making sure to give it a decent berth. About 2.5 miles south you’ll find Thomas Point Lighthouse, a classic screwpile structure and Bay icon that was originally constructed in 1875. Once you’ve cleared Thomas Point, turn southwest to intersect flashing green buoy “1A” at the entrance to the West and Rhode rivers, making sure to clear the shoal at flashing red “2” as you head in.
The Rhode River is the place for cruisers who want to anchor out and enjoy some relative peace and quiet. You can reach it by turning west-northwest from flashing red “2” at the confluence of the Rhode and West rivers to flashing red “2RR” at the mouth of the Rhode. Upriver, just past flashing green “7” is a large, round section of water punctuated with a shallow three-foot-deep spot in the middle. There are a few marinas around, but you’ll need to call ahead to reserve your space and/or make sure they take transient guests.
If you’re interested in exploring the relatively quiet town of Galesville, head into the West River by cruising west from flashing red “2” to green daybeacon “3,” and then following the well-marked (but curvy) channel into Galesville. Councillors Point at flashing red “6” is where you’ll find Pirates Cove Marina, West River Fuel Dock, and West River Yacht Harbor. Upriver from Councillors is Hartge Yacht Harbor, which can facilitate repairs and offers transient slips in a quiet setting.
Farther south-southwest from Councillors Point is Hartge Yacht Yard, which has transient slips and moorings and a full-service boatyard. If you’re hungry, you can get an excellent meal at Pirate’s Cove Restaurant, or you can walk just past Main Street to Thursday’s Steak and Crabhouse, which is a lively gathering place with dock space. If food isn’t on your mind, take a walk around this quaint, quiet, Western Shore town. Or just have a seat at the waterfront and watch the activity in the river.
Day Three: St. Michaels (NOAA Chart 12270)
There’s a ton to like about St. Mikes (as the locals call it), which means this popular Bay place can get quite hectic during holidays and weekends. If you’re able to run your cruise starting during the week versus the weekend, you can avoid some of the hustle of the weekend crowds. But if you crave some action, St. Michaels is well-equipped to handle large influxes of visitors. Ashore, there are more than enough attractions, restaurants and bars, and shopping to keep you and your crew busy.
From Galesville, you’ll want to leave the West River toward the northeast, making sure you leave flashing red “2” to port, and flashing green buoy “1A” to starboard before setting a course for flashing green buoy “1” to the east. Next, head about six miles to the southeast where you’ll see Bloody Point Light, an old, red caisson lighthouse. From Bloody Point Light, make sure you clear flashing green bell buoy “1” to the southeast before turning northeast toward flashing red buoy “4” north of Tilghman Point. A turn toward the south will line up the navigation marks leading to St. Michaels, which is about five miles down the Miles River. Flashing red “4” marks the point off Haul Creek near St. Michaels before you go between flashing red “2” and green daybeacon “3,” leading into the harbor.
St. Michaels Harbor (where you’ll find much of the action) is toward the southwest from the Miles River. Marking the northern side of the harbor is the Chesapeake Bay Maritime Museum (CBMM) at Navy Point, which is easily identified by its red-roofed buildings and Hooper Strait screwpile lighthouse. Transient slips are available for museum members. Many other marinas including Bob Pascal’s St. Michaels Harbour Inn Marina & Spa, St. Michaels Marina, and Higgins Yacht Yard (with service and haul-out) line the rest of the harbor.
The northern branch of St. Michaels Harbor offers spots to anchor, but is exposed to the north and east. The southern branch has an anchorage east of Parrott Point closer in to town, which is somewhat better protected, but it fills up quickly and can be crowded. Water taxi pickup from the anchorages is available by hailing “St. Michaels water taxi” on VHF Channel 71.
If you’ve got a few hours free, there’s no better place to take a walk and explore than CBMM, which has many interesting interactive displays. If you’re hankering for a bite to eat, the Crab Claw is a popular institution right on the waterfront next to CBMM. Farther in town are microbreweries, pubs, coffee shops, and all sorts of restaurants with a number of different cuisines to suit most any taste. Walk to Talbot Street to find the action.
Day Four: Oxford (NOAA Charts 12270 and 12266)
Oxford frequently is referred to as a quieter, more peaceful option for boaters who want a break from the hustle and bustle of St. Michaels. Situated off the Tred Avon River (off the Choptank) on Town Creek, Oxford has an appealing simplicity and an old-town feel. While you may not find dozens of bars and restaurants, or docks filled with transient guests here, you will feel like you’re getting away from it all in Oxford.
The last day of this cruise is best started early, since the journey from St. Michaels to Oxford is either 27 or 35 miles (depending on whether you run inside Poplar Island or outside in the Bay). From St. Michaels, reverse your arrival course back out into the Miles River, out past Tilghman Point, and then to red nun buoy “2” where you’ll turn south into Poplar Island Narrows (controlling depth of six feet).
Once you’ve cleared the southern channel of Poplar Island Narrows, set a course for flashing green “1,” which marks the entrance to Knapps Narrows (four to five-foot controlling depths). After you’ve cleared the Knapps Narrows Bridge (opens on signal), follow the marks out into the Choptank River toward the southeast and quick flashing red buoy “12A” southwest of Benoni Point. Off to the northeast is flashing green “1”, which marks the shoal at Benoni Point and leads you into the Tred Avon River.
To Starboard as you enter is Bachelor Point and Campbell’s Bachelor Point, a full-service marina. Farther north is Pier Street Marina, which has seafood and local dishes available at its restaurant, The Masthead. Upriver, turn east at flashing red buoy “2” toward quick flashing red “2,” which will guide you into Town Creek and Oxford-proper. Marinas abound everywhere.
Among them are Cutts & Case Shipyard, Campbell’s Boatyard at Jacks Point, Mears Yacht Haven, Oxford Boat Yard, Hinckley Yacht Services, Oxford Yacht Agency, and Schooners Landing. You can also anchor out in the Tred Avon River (weather permitting, it is open and exposed), or where room permits in Town Creek, but you’ll need to wrangle your own dinghy ashore since water taxi service is not available.
Oxford is a walking and relaxing town and has an expansive waterfront park overlooking the Tred Avon. Eats are available at the aforementioned Masthead, but Pope’s Tavern also comes recommended. Latitude 38 is small and quaint (but good) just out Oxford Road and Schooner’s has a waterfront vibe. If you’re in the mood for a break ashore, Oxford is home to about a half-dozen bed and breakfasts, all within walking distance to the waterfront. The Oxford-Bellevue ferry is a popular attraction here and offers pedestrian fares of $5 round trip. The ride is an excellent opportunity to see a quick glimpse of the Tred Avon River to the town of Bellevue, just across the river.