Love Point on Kent Island was a haven for vacation goers, lovers, and others just looking to get away. Travelers to Ocean City and Rehoboth would use this access point to their final destination. People would visit from far and wide to relax and bask in the natural beauty of Maryland’s Eastern Shore. This most romantic location flourished for about 50 years before improved roads and the Chesapeake Bay Bridge ended the magical era. A portion of my writing for this was derived from the memories and research of several wonderful local authors: Brent Lewis, Nick Hoxter, and Janet Freedman. They are all well deserving in the thanks and recognition given and I highly recommend their books.

Now, I want you to picture this in your mind’s eye. It is Saturday, July 4, 1914. Railroad tracks run across the island from the Kent Narrows to its most northern terminus at Love Point; a bustling amusement area full of vibrant life, laughter, and excitement overlooking the mouth of the shimmering Chester River. Here, visitors congregate, arriving not only by rail and automobile from the East, but also by water from the West; the West being Pier 5 on Light Street in Baltimore. You can hear the screeching steel of the train coming to a halt at the pier and the howl of the steam whistles pulsing from the Smokey Joe and the Westmoreland, the two most admired ferries of the time. 

As you stand on the giant 100 foot wide and 1,250 foot long ferry pier looking around, you notice all sorts of places to stay and things to do. Closest to you, near the railroad tracks sits Rudy Messerschmidt’s restaurant, bar, and dance hall, a favorite first or last stop for travelers. Looking towards the Chesapeake Bay, there are children building castles on a sandy beach leading into the Chester River where others are relaxing and bathing. If you look a little further, you can see the famous Love Point Lighthouse whose mission is to alert ships entering the channel of the Chester. A spinning Ferris wheel and merry-go-round, up the shore from the beach, entertain children and adults alike. 

Immediately south of the railroad tracks sits a house in the marshy area; the owner of which is renting small rowboats, moored right off the shoreline, for exploring the surrounding waters. Up on the hill, at the curve in the oyster shell road, just a short walk from the pier is the massively magnificent Hotel Love Point, serving the Eastern Shore’s finest menu and entertainment. Directly behind it sits another place to lay your head called Hotel Fillmore. Even further up the shelled street, is a post office, and at the intersection of Love Point Road is Doc Mark’s Store where you can stock up on all the necessities. 

To the north of the hotels and back down the hill is Lake Mattapax where adventurers and fisherman alike paddle canoes while soaking up the scenery. The Picnic Grove sits on the bank of the lake scattered with a variety of trees where you can escape from the sun. The sudden sound of an approaching engine in the sky alerts you to the biplanes flying overhead while an occasional parachuter floats back to Earth. 

Later, a thundering fireworks display rivaling the best in the area will compete with the nearly full moon to see who can better light up the star filled night sky. After the fireworks finale, everyone will make their way to the dance hall at Hotel Love Point where an eight-piece orchestra will be performing all the latest hits until midnight. Then while most make their way to their rooms for some much needed slumber, at least a few love birds will venture outdoors and romanticize under the dark blanket of night, awaiting the dawn of the new day. This was Love Point on Kent Island in the early 1900s. 

The most known and popular attraction in the area was the previously mentioned Hotel Love Point. A grand hotel it was, having three stories, 50 rooms, and everything within furnished to the nines. The expansive and spacious front porch was used by many to relax and chat while observing the hustle and bustle taking place all around. On a typical weekend, the 200 seat dining room would serve up a thousand Eastern Shore meals along with the hotel’s all-you-can-eat buffet. The kitchen offered a variety of foods including the obvious local favorites such as crabs, fish, in season oysters, corn on the cob, and fried chicken. 

Many people ventured through the hotel, together with a few well known individuals. In 1908, the US Clay Pigeon Shooting Championship was held here while the shooting took place in a ravine just up the shoreline. A large crowd watched Lester German of Wilmington, DE win the title. The legendary Annie Oakley, also known for her gun handling skills, was a guest at the hotel that day as well. There was a famous bull thrower named Chad Link that was said to be made of steel. Link used to wrestle bulls in Anne Arundel County and was brought to the hotel for a special event. I guess Link wasn’t used to the Eastern Shore bulls because that day he met his match. The bull provided by Isaac Grollman of Stevensville was so big and mean that it not only threw Chad Link, but also kicked the ring apart and scattered the spectators!

There were multiple tracts of land originating from Love Point Farm, as well as land owners in this area, making the exact date of Hotel Love Point’s construction difficult to nail down. From what I can gather, the original south section appears to have been built sometime between 1890 and 1900 by either Hugh L. Pope or a “Mr. Frew” and was called The Casino Hotel. Then a few years later, The Hotel Love Point Company purchased it and built the north section addition, creating Hotel Love Point. The addition was quite grand in itself: adding parlors, as well as smoking, reading, and writing rooms. The inclusion of several amusements also took place at this time, producing a carnival-like atmosphere. On a deed dated January 16, 1915, I found a list of improvements on the grounds: a dancing pavilion, amusement buildings, bath houses, picnic ground, and beach front. It was advertised as “Maryland’s Grand Old Hotel” which appeared to be quite fitting.

Prior to these hotel additions, there was not a public road leading to the area, only a railroad. Directors of another land owning outfit, The Love Point Beach and Park Company, asked the Queen Anne’s County Commissioners to open a public road to the train station. They made the point that there is a post office and a public landing without a public highway to reach it. This made sense and the deed was done, opening up a brand new opportunity for local residents. Romantic anniversary dinners and day trips to Baltimore would now be accessible without the necessity of a train ride. 

Unfortunately, time has a way of not only creating the new, but destroying the old. Like the saying goes, nothing stays the same forever. In the 1940s, with the dawn of improved roads and the new Chesapeake Bay Bridge in sight, traffic to Love Point slowly dwindled eventually ceasing altogether in lieu of a faster route to the beaches of the Eastern Shore. The last ferry pulled out of the Love Point pier on August 31, 1947, carrying only a handful of foot passengers and cars. 

Hotel Love Point also closed its doors in 1947. For 18 years it sat empty and abandoned, rotting away in the field that was once full of life and energy. Abused and vandalized for years, it finally met its maker in November of 1965 when it mysteriously caught fire and burned to the ground. The end was as grand as the beginning as the blaze engulfed the structure with a ferocity and the smoke from the fire could be seen for miles. In just an hour, Hotel Love Point was gone. 

Not much is left at the once bustling site. If you visit the end of Pier Road you can still see and quite possibly feel the presence of a time once lived and loved. On the north side of the road, after you come around the bend there are two open areas. The first one belonged to the most recently removed Hotel Fillmore. The next, bordering Lake Mattapax and overlooking the Chester River, belonged to Hotel Love Point. On the south side of the road, as you approach the current Department of Natural Resources (DNR) gate, you can see a gully bordering the woods where the railroad tracks ran. These tracks, owned by The Queen Anne Railroad Company, linked Love Point to Stevensville, Chester, Queenstown, and all the way to Ocean City. 

Near the Chester River lies the bones of the train and ferry pier, along with the current DNR office building which was Rudy Messerschmidt’s establishment and later became the Anchor Inn. C.J. Langenfelder and Sons purchased all the tracts of land in 1963 and sold it to Langenfelder Marine in 2002 to operate their marine contracting business, reusing and modifying the original pier. In 2007, the State of Maryland purchased the property to be used by the DNR and eventually be turned into a state park. 

It was a romantic and magical time for Kent Island and remains nostalgic for many old-timers. My grandmother, Donna May Bryan, is especially attached. She recalls her aunt Addie C. Knight and uncle Jospeh W. A. Evans moving their restaurant to Hotel Love Point in 1934 and operating the kitchen for the dining hall. She also remembers sitting in the wicker chairs on the enormous front porch, overlooking the vast grassy lawn and Chester River. If you visit on a breathless, still day, and listen to the rhythmic lapping of the water on the beach, you may just be able to hear the spirits of a time lost having the time of their lives.