Chesapeake Beach, a town envisioned as America’s Monte Carlo back in 1900

4 things to do in Chesapeake Beach today

… Estimated reading time 16 minutes —   This time I am in a train called the Chesapeake Beach Railway on the way to Chesapeake Beach, Maryland, located on the Western shores of the Chesapeake Bay.

As our avid readers know, this blog is about pleasure boating, coastal living, travel, and lifestyle. My wife and I are boaters, rediscovering coastal towns on the way to our Slow Boat To Florida journey on the Atlantic Intracoastal Waterway (ICW) with our 26’ SeaRay Sundancer, Life’s AOK. However, the spirit of this blog is to not assume everyone may have a boat. If you have a boat, that is great! Also, if you are a boating enthusiast and appreciate boating, that is good enough for us. That’s because all of the locations that we visit are accessible by boat as well as by car. For the sake of this particular blog post, let’s add a train as well, why not? As long as you can arrive at any location that we write about by boat or by land, any means would work. Also, as my regular readers know, I love time capsules — even if it is momentarily, it forces our imagination, transports us to a different era, and gives us interesting insights into locations we are visiting in the 21st century. We see what and how much has changed.

From Union Station to Chesapeake Beach

Back to our train, it left Union Station in Washington, DC at 10:00 a.m.  Within 30 minutes, we reached Upper Marlboro, Maryland.  After passing a few more stations, like Mt. Harmony and Pushaw, we are expected to arrive in Chesapeake Beach, Maryland at 11:15 a.m. The lure of this particular train for us was that the coach’s windows and doors were entirely screened for a clean, cool, and comfortable ride. Before the addition of the screens, one passenger remembered that, when he was a boy, it was “the dirtiest train that you could conceive of” because it was a short train, meaning cinder from the engine flew into the cars.  

Photo courtesy of Chesapeake Beach Railroad Museum

Well, the train and the ride that I was imagining was real, back in the 1900s. The town of Chesapeake Beach that was created as a ‘resort’ was envisioned by the builder and Colorado magnate Otto Mears as an “American Monte Carlo.”  That is when the story of Chesapeake Beach started.

That was then

Mears started in the late 1890’s. He was an independent, short-line railroad builder from Colorado. He and a group of Denver associates designed Chesapeake Beach as a resort town, complete with beachfront hotels, a race track, casino, bathhouses, and beaches. A 1,600-foot boardwalk was built over the water, and a 21st-century version is still there. A mile-long pier (a new version of it still there) was built to receive passengers arriving daily by steamer (passenger steamboats) from Baltimore in the summer months.

Arriving daily passenger steamboats arriving from Baltimore. Photo courtesy of Chesapeake Beach Railroad Museum

Finally, the Chesapeake Beach resort officially opened on June 9, 1900. From 1900 until 1930, people would mainly come for day trips by railway and steamboats like “The Dixie” and “The Dreamland.” Only 28 miles from Washington, D.C., people with more leisure time would flock to Chesapeake Beach for the cool breezes and saltwater. The resort was connected to the Eastern Shore of the Chesapeake Bay by a boat to Oxford, Maryland.

The luxurious Belvedere Hotel that was

Overnight visitors could stay in the luxurious Belvedere Hotel, which was built about 1900. It was located on the north side of 17th Street overlooking the Bay before it was destroyed by a fire on March 30, 1923. Today, a group of townhomes are located at the same site. 

The famous Belvedere Hotel, which was built about 1900 in Chesapeake Beach. Photo courtesy of Chesapeake Beach Railroad Museum

The resort consisted of a boardwalk over the water and a pleasant park and picnicking area on the nearby land. On the boardwalk, one could find a bandstand (or bandshell), a dance pavilion, performing bears, games of chance, a carousel, casino, theaters, and many restaurants. A roller coaster, called “The Great Derby,” was constructed over the boardwalk about 1900 and operated until the late 1920’s. 

Chesapeake Beach and the next town over, North Beach, grew up together in conjunction with the resort.

A roller coaster, called “The Great Derby”. Photo courtesy of Chesapeake Beach Railroad Museum

The Great Depression hits the town

The Great Depression, the worst economic downturn from 1929 to 1939, and the growing popularity of the automobile spelled the end of the railroad and the grand dreams of America’s Monte Carlo, also billed as Washington, DC’s Coney Island. Along the way, life still went on and even thrived to a degree.  Wesley and Elizabeth Stinnett opened a cozy, bayside restaurant named Stinnett’s in 1936. That was a year after the railway line between Chesapeake Beach and Washington stopped running. The closure of the 27-mile railroad also put an end to the town’s booming tourism industry, which had — in its heyday — drawn thousands of visitors to its mile-long pier lined with games, restaurants, and a roller coaster. Along the way, America’s love of cars grew and… grew.

More challenges await

Then the Chesapeake Bay Bridge opened in 1952.  Now, motorists could reach the Eastern Shore as well as Atlantic beaches, such as Atlantic City, so much faster than by driving all the way around the Chesapeake Bay and being forced to stop for lunch along the way.

This significant loss of traffic was further compounded by the ending of Maryland’s legalized gambling in 1967, leading to the decline of Chesapeake Beach, along with its twin town, North Beach. However, life still went on. Then on September 19, 2003, Tropical Storm Isabel passed through extreme western Maryland. The worst of its effects came from its storm surge, which inundated areas along the coast and resulted in severe floods and beach erosion. Chesapeake Beach — including Stinnett’s — took its share of misfortune from Isabel.

“In the weeks after Tropical Storm Isabel swept through, the question lingered in the salty air over Chesapeake Beach. Everyone, it seemed, had a theory about the fate of the cozy, 67-year-old bayside diner, its interior destroyed by flooding from the storm.

“It was not until this month, after much deliberation, that brothers Gerald and Fred Donovan came to a difficult decision. So difficult, Gerald Donovan said, that they could not deliver the news in person.

Instead, they took out a full-page announcement in four Calvert County newspapers. ‘Thanks for the memories,’ it read. ‘Now, it is, unfortunately, time for us to close our doors. This is the end of an era for us.” The Baltimore Sun, November 24, 2003

Full circle

Since its start over a century ago based on Colorado magnate Otto Mears’ plan of the late 1890s, Chesapeake Beach has come full circle.

A newspaper advertising from the 1900s

Its initial vision was resurrected, in a scaled-down and updated version, in 2004. The Chesapeake Beach Resort and Spa was born, recapturing the original intent of the founders of this small coastal town to have a bayside resort just close enough to Washington, D.C., Baltimore, Annapolis, and the surrounding areas. It is now called Road ‘N’ Reel Resort.

4 things you can do in today’s Chesapeake Beach

First, if fishing is one of your favorite sports, prepare not to be disappointed. There is a very good chance that you will catch a lot of fish rather than have the captain keep throwing “chum” into the water and you getting nothing out of your trip.  There are a few fishing charter boat companies that are well prepared to deliver the goods for you. Katherines Charter Fishing, along with Rod ‘N’ Reel Resort’Fishing Tour Aboard Miss Lizzy, or Daydreamer Sport Fishing are some that you can consider.

Miss Lizzy. Photo courtesy of Rod ‘N’ Reel Resort

Second, if you want to just relax and take it all in on the water, a few sailboat cruises are there to satisfy you. Just let the Bay seduce you and put a smile on your face while sailing with  Chesapeake Windsail Cruises.  They have a number of types of cruises that will satisfy your expectations.

Third, another option is doing nothing. To me, that is truly a great option. Perhaps it’s the right time for you to downshift your internal gears, slow down, and remember why you visit small coastal towns. Whether your arrival was by boat or by land,  Rod N’ Real Resort is well-positioned to provide you with modern creature comforts. All you have to do is just remember: you are there to relax and unwind, to get away from it all.  Doing nothing is a good option, really.

Rod ‘N’ Reel Resort

However, you have a right to have fun, right?  Who can argue with that? Well, fourth, if boredom visits you, then you can visit the small but family-friendly Chesapeake Beach Water Park nearby. Another option is to walk over to the Chesapeake Beach Railway Trail, by yourself or arrange a guided tour. I also want to say that you can visit the Chesapeake Beach Railway Museum, but at the time of this writing,  this charming small museum is scheduled to be closed for renovations until further notice. If calmly walking around is all too slow for you, you can ramp up your pace by renting Jetskis at DMV Jetskis and go out there and have fun.

If that is not enough for you and you are still missing city life, just have a day trip to nearby Washington, DC, Annapolis, or Baltimore. Chesapeake Beach is strategically located near all three towns. Washington, DC, with all its glory, is less than an hour away,  Annapolis is 40 minutes, and Baltimore about an hour.  

Herrington Harbor South, a great getaway on the Bay

If you are traveling by boat, with any size of vessel up to a superyacht, this is the resort marina where you want to stopover. Before 1978, 30 minutes north of Chesapeake Beach, in the town of North Beach, there was the Rose Haven Marina.  Today, it has been vastly enlarged and renamed Herrington Harbor South. It is a boater’s and visitor’s destination that you should not miss. It is considered one of the premier resort-marinas on the East Coast and another gem of the Chesapeake Bay for boaters.

Herrington Harbor South. Photo Courtesy of Harrington Harbor

It’s a luxurious marina resort, complete with all the amenities of a fine getaway on the Chesapeake Bay. Their protected marina basin has 600 boat slips and everything a recreational boater could desire. Amenities include a lighted tennis court,  basketball, pickleball, fitness center, and sauna, complimentary kayaks and paddleboards, beach and lawn games, and seasonal water fitness activities. Resort facilities include coin-operated laundry rooms, dinghy rack storage, storage lockers, and 24-hour ice availability. They also have outdoor amenities, with an Olympic-size pool with kiddie pool, private beaches, picnic areas with grills, garden areas, and a playground. Dining facilities include the Ketch 22 Restaurant, Chesapeake Market & Deli, and Herrington on the Bay Catering.  On the entertainment front, they have outdoor movie nights, cable TV, and free WiFi internet service. By land, you can visit Annapolis, 30 minutes away.

The Inn at Herrington Harbour

Herrington Harbor South houses a lodging gem, The Inn at Herrington Harbour, that may surprise you. You can enjoy a picture-perfect setting framed with beautiful gardens, meandering paths, courtyards, and splendid water views across their private sandy beach.

The Inn at Herrington Harbour. Photo courtesy of Harrington Harbor.

The relaxed comfort and style of the Inn is reflected in an Art Deco design, authentic furnishings, and unique touches that include soaring windows, stone fireplaces, hardwood floors, and artisan tiling. ​

Herrington Harbor North

Herrington Harbor North is complete with another set of 600 boat slips, first class haul-out services, land storage, on-site marine contractors, and brokerages. It’s the perfect combination of a marina-resort and full-service yacht center.  The North facilities are capable of servicing any vessels up to large superyachts on the way from New York to Florida on the Bay. 

We plan to visit and cover Herrington Harbor South and North as a part of our Slow Boat to Florida series.

Well, that’s it for now. Stay well. I hope to say hello to you if you spot my boat, Life’s AOK, in one of the locations that I’m hoping to visit in 2020, that is if Coronavirus permits us.

I bid you Fair Winds and Following Seas.

1 thing I learned

  • Showing human spirit and determination, the resilience of Chesapeake Beach and its twin town, North Beach, is exemplary.  Despite the fact of multiple setbacks in their towns’ histories, the towns are still here and thriving. People who make that possible remind me of a great quote from Wilma Rudolph: “Never underestimate the power of dreams and the influence of the human spirit. We are all the same in this notion: The potential for greatness lives within each of us.”  Who was Wilma Rudolph? She was a sickly child who had to wear a brace on her left leg due to polio. She overcame her disabilities to compete in the 1956 Summer Olympic Games, and in 1960, she became the first American woman to win three gold medals in track and field at a single Olympics. See more on her in a Sports Illustrated article.

1  thing I recommend

How easy?

Marinas where you can tie up your boat

Stay safe.

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