Walking the Kent Island Railroad

“Kent Island’s howling trains and sprawling tracks may be gone, but when I walk the Cross Island Trail, I feel them—echoes of steel wheels on iron rails.”
- J. Coursey Willis

If you’ve ever wandered the Cross Island Trail between Old Love Point Park and Gibson’s Grant, you’ve walked the bones of Kent Island’s railroad past. This stretch of trail—two miles, running east to west—traces the rail bed that once connected the Stevensville and Chester stations. Back then, a line of steel cut across the island from Love Point to the Kent Narrows, but only this piece of history repurposes the path.

It all started in February 1894, when the Maryland Legislature gave the Queen Anne’s Railroad Company the green light. Their mission was grand: lay 60 miles of track, linking Baltimore, MD, to Cape May, NJ, through the heart of the Eastern Shore. The line came together piece by piece—first connecting Queenstown to Denton on July 15, 1896, then extending to Greenwood, DE, by New Year’s Day, 1897, and finally reaching Lewes on March 1, 1898. The steamboats—Smokey Joe anWestmoreland—handled the rest, ferrying passengers and goods across the water. These trains weren’t just moving people—they were lifelines, opening new markets for seafood, crops, and produce from the Shore.

In February 1902, the railroad reached Kent Island, laying the final 12.9 miles from Queenstown to Love Point. At the end of Pier Avenue, the tracks met the Chester River, where ferries were waiting to shuttle passengers to Baltimore. Love Point was a destination of its own—a getaway where majestic hotels like Love Point and Fillmore stood, casting long shadows over nights spent in summer’s magic. For the young and restless, Camp St. Martin offered amusements, while the ferry ride promised adventure for everyone else. For a dollar, you could travel from Love Point to Lewes in just under two and a half hours.

At Love Point, the train turned around on a triangular track—called a “wye”—and headed south. It followed the edge of Love Point Road, then curved east where Kent Island High School now stands. Where the two Love Point roads split, passengers arrived at Stevensville Station—the heart of the island’s railroad operation. The station hummed with life: a ticket office, a telegraph operator tapping out messages from the bay window, a freight house with scales, and a maintenance shop. Behind the station, passengers hitched their horses and waited for the next ride out, while kids sneaked glances at the busy platform.

From Stevensville, the train pushed southeast along today’s Cross Island Trail. One landmark still standing is the bridge over Cox Creek—its pilings relics of the original trestle. During the blizzard of 1911, snow buried the tracks here so deep it took days to dig the train free. That trestle stood until the trail opened on August 22, 1998. Beyond Castle Marina Road, the tracks veered off, shadowing Piney Creek Road until meeting back up by the Four Seasons water tower. Where the trail turns south, crossing a bridge, the train kept going, passing through what’s now a chain-link fence and stopping at Chester Station near the headwaters of Macum Creek.

The line carried on another 2,000 feet, cutting through marshland before crossing Route 50 near Whites Heritage Lane at Gibson’s Grant. It ran parallel to the highway until Exit 41, where it drifted east through the marshes of Piney Creek, lining up with Medic Drive and crossing the Kent Narrows railroad bridge. Some of those old pilings still rise from the waters, holding on like ghosts from another time.

If you follow Medic Drive to the end of the Watermen’s Boat Basin, you’ll find the remains of the old railroad bridge. This wasn’t just any bridge—it was mounted on a hand-cranked turntable, run by my great-grand uncle, Joe Bryan. When trains needed to pass, Joe would crank it shut—if they could find him. According to my grandmother, Donna May Bryan, Joe spent a bit too much time at Bill’s Tavern (now Angler’s), just east of the Narrows. The Kent Narrows Station sat close enough to the bar that you could almost hear the telegraph tapping through the clink of glasses.

The original Route 18 drawbridge once spanned the Narrows, 200 feet south of the railroad bridge. What’s left of it lingers quietly at the end of Wharf Drive. And if you ever find yourself standing by the bathrooms at the Big Owl Tiki Bar, take a moment. You’re standing dead center where that old drawbridge used to touchdown, where cars and wagons rolled through on their way across the water.

From there, Route 18 snakes east, past the last of the five 1902 railroad stations at the end of Station Lane in Grasonville—once known as Ford’s Store and Winchester. Beyond that, the tracks pressed deeper into Queen Anne’s County, connecting small towns with names that carryon: Queenstown, Centreville, Bloomingdale, Wye Mills, Willoughby, and Queen Anne—the last stop before the line met the Delaware & Chesapeake Railway.

Trains traversed the island twice a day, hauling passengers, freight, mail, and newspapers hot off the presses in Baltimore. Every now and then, an express line or special excursion would roll through, stirring up excitement. That 1902 track was a lifeline, but good times don’t last forever. Trouble was already closing in, waiting just around the bend.

Winters were brutal out here. In 1903, the bay froze solid, shutting down ferry traffic for almost a month. Then, the Great Baltimore Fire of 1904 scorched the city’s commercial district. Without Baltimore’s business, the Queen Anne Railroad was as good as done. On January 27, 1905, it was sold to the Pennsylvania Railroad—“The Pennsy,” the most powerful railroad in the world, with a budget that rivaled the U.S. government.

The Pennsy didn’t stop with the Queen Anne’s Railroad. It swallowed the Weems line of steamers and the Chester River Steamboat Company too, merging all three into the Maryland, Delaware & Virginia Railroad Company (MD&V) under the control of the Baltimore, Chesapeake & Atlantic Railway (BC&A). Locals had their own names for them—Muddy, Dirty & Vicious or Black Cinders & Ash.

That four-million-dollar deal gave the Pennsy full control over every transportation route on Maryland’s Eastern Shore. But out here, things didn’t run like they did on the Western Shore. Small towns dotted the lines, and business ebbed and flowed with the tourist seasons, making it tough to turn a steady profit. The numbers didn’t add up, and by May 1923, the Pennsy started cutting its losses, selling off chunks of the MD&V. The 30-mile stretch from Denton to Love Point was folded into the Baltimore and Eastern Railroad (B&ERR), another cog in Pennsy’s machine.

As cars took over, commuter trains fell out of favor, and Kent Island leaned on ferries from Matapeake and Romancoke to stay connected. On January 14, 1938, the B&ERR asked to shut down passenger service between Easton and Love Point. Islanders fought back, traveling to Baltimore to argue for their livelihoods, but it didn’t matter. On March 29, 1938, the last passenger car pulled into Love Point, leaving only a tri-weekly freight service behind.

By the 1950s, the Chesapeake Bay Bridge loomed, and the railroad’s fate was sealed. On August 1, 1947, the B&ERR ended ferry service from Baltimore to Love Point. The freight line limped on, hauling construction materials to build the bridge that would seal its own fate. When the bridge opened in July 1952, the ferries disappeared, leaving one way to cross the bay.

On January 17, 1956, the Pennsy went before the Interstate Commerce Commission, asking to scrap the freight line between Love Point and Queenstown after running at a loss for three years. The tracks west of Kent Narrows hadn’t seen a train since October 1954—deemed unsafe and abandoned to time. Despite a petition from the Tidewater Chamber of Commerce, the line officially ended on June 25, 1956. Progress won.

The Stevensville Station is the last remnant of Kent Island’s railroad days, saved by the Kent Island Heritage Society in 1987. Today, only a freight line between Carville and Massey still runs in Queen Anne’s County, miles from the island. Kent Island’s howling trains and endless tracks may be gone, but when I walk the Cross Island Trail, I feel them—echoes of steel wheels on iron rails. I see the island through the eyes of a 1930s passenger, taking it all in—an echo of something lost but not forgotten. A beautiful, fleeting vision.

Kent Island’s howling trains and sprawling tracks may be gone, but when I wander the Cross Island Trail, I feel them—echoes of steel wheels on iron rails. I see my home through the eyes of a 1930s passenger, taking it all in—a reflection of something lost but not forgotten. A romantic, fleeting vision.

Resources:
3/19/1891 - The Republic - Tie and Rail
10/11/1904 - The Pittsburg Press - Purchased By Pennsy
1/14/1905 - The Democratic Messenger - Maryland Delaware and Virginia Ry. Co.
2/8/1905 - The Smyrna Times - Pennsylvania Railroad In Control
5/17/1928 - The Pittsburg Press - Pennsy Petitions
1/21/1938 - The Star Democrat - Public Service Commission of Maryland Order No. 31752
1/21/1938 - The Star Democrat - Hearing On February 10
2/4/1938 - The Star Democrat - Love Point Train May Be Withdrawn
3/5/1938 - The News Journal - Queen Anne's 'Iron Horses' Finally Bows to Autos, Buses
3/6/1938 - The Baltimore Sun - End of Train Service to Force Mail Change
3/30/1938 - The Baltimore Sun - Train Makes Last Trip on Eastern Shore Run
3/6/1947 - QA Record Observer - Proposal to Stop Ferry Brings Number of Protests
8/21/1947 - QA Record Observer - Ferry to Stop
3/17/1953 - The Evening Sun - Rail Lines on Shore Recalled
3/15/1956 - QA Record Observer - Railroad to Abandon 12.6 Miles
5/30/1956 - The News Journal - Railroad Gets Okay to Abandon its Line Serving Kent Island
1/12/1967 - KI Bay Times - I Remember the Muddy, Dirty, and Vicious Says Franklin Marion Crouse Lewis, Agt
4/14/1988 - Chesapeake Courier - Last Love Point to Easton Run Made in March, 1938
7/13/1989 - KI Bay Times - Railroads Are A Lasting Fancy
12/16/1992 - KI Bay Times - Rails Put County On Road to Resorts in 1897
4/5/2006 - KI Bay Times - Steamboats, Trains Were the Way to Go
Various Articles Written By The Kent Island Heritage Society

Pictures Courtesy of:
The Kent Island Heritage Society
The Queen Anne's Railroad Society
Historic Kent Island Private Collection