When Capt. John Smith came up the Chesapeake in 1608 and rounded what is now Howell Point into the Sassafras River, he was met by dugouts filled with armed Tockwogh warriors. Although he had been trading with Iroquois raiders, the Tockwoghs’ mortal enemy, the locals thought he had been fighting the Iroquois, and he did not attempt to convince them otherwise, making friends. It may have been then that the saying “Relax, you’re on the river,” was born, and to this day it remains good advice, particularly in the fall.
Although dugouts are long gone, boating is still popular on the Sassafras, and sailboats, powerboats, kayaks, canoes and even the occasional buyboat can be seen in all seasons. When you travel to the river on the Chesapeake, stay to the east of the shipping channel and keep alert because car ships, container ships and tug/barge combinations travel regularly between the Chesapeake and Delaware Canal and Baltimore.
A well-marked channel on the Sassafras will guide you inland. A local mariner recommends that when you enter from the South, “Aim for red buoy No. 2, and you’ll have 10 to 20 feet [of water depth] along the way toward Turner’s Creek; then bang a right, head for the bluffs ahead, and you’ll have plenty of water.”
Past Turner’s Creek the river gets shallower, and there are underwater obstructions to watch out for as it serpentines past Money Creek. Numerous creeks enter along the length of the river from the north and the south, almost all of them less than 5 feet deep.
When you reach Georgetown, you’ll see the Route 213 bridge across the river. It has a 5-foot air clearance on its best day, but it can be opened with a call to the Sassafras River Bridge tender on channel 9 or 13. (In wintertime, six hours’ notice is required.) Beyond the bridge, the river runs about 6 feet deep for just under a mile and then becomes unnavigable for all but small boats.
British forces visited the Sassafras twice during the War of 1812. In the spring of 1813, Adm. George Cockburn led a squadron up the Chesapeake — including the 74-gun HMS Sceptre, three frigates, two brigs, two schooners and support vessels — to disrupt trade and terrorize the population. After the frigate HMS Maidstone shelled Howell Point, Cockburn’s forces landed at Turner’s Creek, took pilot James Stavely hostage and had him navigate them upriver in search of plunder, with the HMS Mohawk (a brig with a 7 ½-foot draft, recently captured from the Americans off Belize) leading the way.
As they approached Georgetown, the Kent County militia fired on them from Fredericktown on the north side and Pearce Point on the south. Undeterred, the British landed on both sides of the river and put Fredericktown and most of Georgetown to the torch. Two houses were spared, thanks to Kitty Knight, who persuaded Cockburn to leave her residence, and that of an invalid neighbor, intact.
The British returned to the region in the summer of 1814, when the Kent County militia got the better of the invaders. Again in search of supplies, the intruders landed but were observed by locals who reported their movements to Col. Philip Reed, who stationed artillery on the high ground near Isaac Caulk’s cornfield and snipers on the flanks.
As the British approached Caulk’s house, a withering fire killed their commander, Capt. Peter Parker. On one of the few occasions during the conflict when the American militia triumphed, the British retreated to the HMS Menelaus, sailed south down the Chesapeake and a month later were defeated in the Battle of Baltimore.
The locals are a lot more hospitable these days, with facilities for boaters up and down the Sassafras and plenty of activities to keep them peacefully occupied. There are several marinas on the river, including the Georgetown Yacht Basin (with a 110-ton lift) and Duffy Creek Marina on the south side, the Sassafras Harbor and Skipjack Cove marinas in Fredericktown to the north and the Gregg Neck Boat Yard, upriver from the Route 213 bridge.
There are plenty of activities to entice visitors. One of the most successful is the Downrigging Weekend in Chestertown at the end of October, which includes a tall ship and wooden boat gathering focused on the schooner Sultana, public sails, live music, arts and crafts demonstrations, wine tastings and talks by noted historians, authors and naturalists.
Turner’s Creek Park and the Sassafras Natural Resources Management Area, located on the south side of the Sassafras River, four miles east of the Chesapeake, offer a 100-foot pier and a public boat launch. In the 147-acre park visitors will find tremendous views of the bay and river, numerous walking, equestrian and biking trails through groves of white oak and papaw trees, and a variety of waterfowl and songbirds overhead. On the north side of the river, across from its mouth, is the Grove Neck Wildlife Sanctuary, which is principally a wetlands area with hiking, bird-watching and wildlife photography opportunities.
Accommodations in the region include the Kitty Knight House Inn at the Georgetown Yacht Basin on the Sassafras and several more hotels in nearby Chestertown and Rock Hall, Maryland. Eastern Shore cuisine can be sampled at such places as the Kitty Knight House Inn on the south side, Signals Restaurant and The Granary at Skipjack Cove on the north side in Fredericktown and Twinny’s Place on Main Street in nearby Galena.
The Algonquin tribes of Maryland’s Eastern Shore kept track of time by the number of winters they had weathered, which they called cahonks after the call of migratory geese. If you can avoid it, don’t rush south, as the fall colors, uncrowded waterways and hospitable people make the Sassafras a great place to visit after Labor Day. As the locals have been telling people since John Smith cruised in, “Relax, you’re on the river.”
This article originally appeared in the February 2016 issue.