Know your Ocean City Bayside
Last month we highlighted some of the interesting things related to the Ocean City boardwalk such as its true length, oldest building, oldest business, and several other items. Now let’s look at the bayside and into some of its interesting features and trivia. Specifically, this article will speak of the oldest section which is the southern end of our ten-mile island that we call Ocean City.
Oldest Restaurant in Ocean City
Ocean City has several older restaurants that have been around for decades. But the oldest is the Angler Restaurant, located on the bay at 312 Talbot Street, just south of the Route 50 Bridge.
Excerpted from the ‘Our History Heading’ on the Angler Restaurant Website:
“Around the turn of the 20th Century, Charles Rollins Bunting purchased the property where the Angler restaurant now stands. At that time there was no dock, only marsh grass through which the Buntings pulled their sail bateaux and row boats to shore.
In the Winter of 1934, Charles’ son William (one of five sons) returned to Ocean City from North Carolina. A year later, he bought a house and property adjoining his father’s dock. There he built a small 20’x20′ building where he sold fishing bait, cool sodas and rented small boats.
His wife Louise, an enterprising young woman, started selling homemade pies. It soon became obvious that they needed to serve breakfast, lunch and dinner. Small tables were placed in the fishing office and it became a combined business adventure.”
And this started in 1939, thus making the Angler Restaurant 86 years old this year!!
Special note: In 2024, the Angler Restaurant and Bar was voted as best happy hour by public voting in Oceancity.com’s Best of Ocean City® Awards.
Some Facebook comments about the Angler:
Bill G. “I love the atmosphere at The Angler.”
Sherry C. “One of our absolute favorite places in OC! See you soon!”
John C. “Best happy hour in Ocean City!!”
Oldest Bar in Ocean City
Quietly situated at 216 Somerset Street, near St. Louis Avenue in downtown Ocean City is the Harbor Inn bar. Starting in 1935, the same family has owned this business with a long bar, pool table, some tables, and lots of character. It’s fondly known as “the Bloody Bucket,” one of Ocean City’s favorite dive bars.
In 2021 a fire temporally closed this fine establishment; reopening in September that year, stronger than ever.
In January 2025, Oceancity.com did a Facebook post congratulating the Harbor Inn on its ninetieth (90th) birthday coming in 2025. To express the public interest in this bar, this FB post received over six thousand likes, over five hundred shares, and reached almost 900,000 people! Now that’s love!
Just look at several select comments from that Facebook post:
Amy B. “We love the Harbor Bar!! It’s a must for a drink or two on every trip to OC.
Mike P. “My favorite bar in the state of Maryland!
Patty R. “Many good times had in the Bloody Bucket.”
To learn more about this small, but popular bar check out this 2021 article:
Early Transportation into Ocean City
In its early days, people entered Ocean City from the railroad bridge, which connected from West Ocean City to what is now South Division Street (the site now Sunset Park) in downtown Ocean City. This bridge was constructed in 1876. However, The Storm of 1933 destroyed this bridge and ended railroad access into Ocean City. Ocean City had two railroad stations; one along Baltimore Avenue and the other on Philadelphia Avenue, just north of Wicomico Street.
In 1916, a simple two-lane bridge was constructed from Old Bridge Road in West Ocean City to Worcester Street on the island. This small, but important bridge was later replaced in 1942 by the more modern (at that time) bridge know as the Route 50 Bridge or also called the Harry W. Kelley Memorial Bridge. Special note: This bridge contains a draw that opens regularly to allow marine traffic, typically at 25 minutes and 55 minutes past the hour during the peak tourist season (May thru October).
In 1971 the Route 90 Bridge (Ocean City Expressway) was completed that enters Ocean City midtown at 62nd Street. Route 90 runs about 12 miles in length with its eastern end in Ocean City and western end near Whaleyville.
Bayside Fishing Industry
The early days of Ocean City contained pound fishing along the ocean side. On the bayside, Captain Charles Bunting is credited with building a dock at Talbot Street in 1918, adjacent to the site that would eventually be home to the Angler Restaurant. From this space, sailboats and rowboats were rented to anglers to fish the bay. Of course, much changed because of The Storm of 1933, which created the Ocean City inlet and permitted boat access from the coastal bays to the Atlantic Ocean.
Today the Ocean City bayside contains a number of marinas, as does West Ocean City. A number of prominent fishing tournaments are annual events with the largest being the White Marlin Tournament; held in August of each year, starting in 1974. The WMO is the biggest and richest billfish tournament in the world and is based out of the Harbour Island community on 14th Street in Ocean City. Other, more-recently established fishing tournaments are based out of these bayside marinas; such as the Big Fish Classic tournament at MR Ducks on Talbot Street, held in late July, since 2014, and Captain Steven Harman’s Poor Girls Open, which started in 1994 at the Bahia Marina (21st Street), typically held in August – the week following the WMO. Proceeds from this latter tournament are used to benefit breast cancer research. Check out fishinoc.com website for the full list and dates of these 2025 fishing tournaments.
The Coastal Bays
An article about our Ocean City bays would not be complete without additional information about some details. For those not familiar, there are actually five coastal bays in Maryland, but only three of these bays abut Ocean City. These three descriptions from the Maryland Coastal Bays website are:
- Sinepuxent Bay’s drainage includes northern Assateague Island and a narrow strip of the mainland south of Route 50, including the Route 611 corridor and land to the east. It is the smallest of the five coastal bays sub watersheds. The bay receives considerable oceanic flushing from the Ocean City inlet.
- Assawoman Bay’s drainage includes both Worcester and Sussex counties, with over 40% of the drainage in Delaware. The northern half of Ocean City drains to Assawoman Bay. Grey’s Creek is the primary tributary that drains into Assawoman Bay in Worcester County.
- Isle of Wight Bay’s drainage includes both Worcester and Sussex counties, with nearly 15% of the drainage in Delaware. It is the second largest bay and drainage of the five coastal bays, and includes Manklin Creek, Herring Creek, Turville Creek, St. Martin River, Bishopville Prong, and Shingle Landing Prong. The community of Ocean Pines, the southern half of Ocean City and West Ocean City drain to this bay. The bay is bounded to the north by Route 90 and Route 50 crosses the Bay near its southern boundary.
The Newport Bay and Chincoteague Bay are further south from Ocean City.
We hope you learned a little more about the Ocean City bayside from these highlights. There are numerous items of interest found along the Ocean City bayside based upon its history and current activities. Make sure you spend a little time on the “quiet side” of downtown Ocean City on your next visit.
The building that we all know of as the Kite Loft was constructed about 1930, and originally it was Eugenia’s Guest House. It later became Maria’s Guest House and is now the Kite Loft, the shop few can prevent themselves from stepping inside, as there is so much to see, and buy! 
This season, Ocean City is implementing the ParkMobile app for payment at most parking locations. Street and lot parking (excluding the Inlet Parking Lot) now require the app. The Inlet Parking Lot will transition to app-based payment in 2026. If you do not have a smartphone, you can pay online, by phone, or via text. The sign where you are parking will have details on secondary payment options. Download the ParkMobile app before arriving in Ocean City to make your parking experience a lot easier!
Northside Park is Ocean City’s largest park. It has softball, baseball and soccer fields, a fishing lagoon, foot bridge, concession stands, two playgrounds, picnic area, two piers, and a gazebo. It’s host to Sundaes in the Park during the summer on Sunday evenings, and Winterfest of Lights from Thanksgiving until New Year. But in the Springtime, its tranquil beauty really shines through. And if you time it just right, you get to experience the cherry blossoms in bloom, with a lot less visitors than our wonderful DC neighbor!
Built in 1930, this private residence, located just north of 14th Street, carries a unique distinction: when it was built, it was located outside of the city’s limits!
These small cottages are located along St. Louis Avenue in downtown Ocean City. 
On the north side of 6th Street, between Baltimore and Philadelphia Avenues, you’ll find the Johnson-Sanford House, a charming private residence constructed in 1936, boasting a variety of architectural details.
This building, a landmark on the Ocean City Boardwalk at 8th Street, was constructed in 1945 and now serves as Malibu’s Surf Shop, a popular spot for beachgoers. 
The Beach Walk On The Ocean was built in the 1930s and is one of four seaside cottages lining the Ocean City boardwalk between 10th and 11th Streets.
Wilmington Lane, a historic alley that weaves through downtown Ocean City, reveals a glimpse into the town’s past. Running from 4th to 15th Streets between Baltimore and Philadelphia Avenues, and with an additional segment from N. Division to 3rd Street, it continues to serve a diverse mix of residential and commercial purposes.
A prominent landmark on the Ocean City Boardwalk at the Inlet, the Ocean City Life-Saving Station has a rich history. Constructed in 1891, it was originally located on Caroline Street before being moved to its present location on the Boardwalk in 1977.
This architecturally detailed house is located at the corner of Philadelphia Avenue and 6th Street.
Imagine Ocean City in 1930, when 707 Wilmington Lane was the bustling Ocean City Dairy, delivering fresh milk to local families. Today, this building, transformed into apartments in 1950, stands as a charming reminder of the town’s past.
Built in 1877, St. Mary Star of the Sea Parish was the first Catholic Church in Ocean City, Maryland. In 1880, it was one of only three non-residential structures, a solitary presence along the sandy expanse of what would become a bustling beach town.
Another view of Wilmington Lane, this time near 10th street.
Looking along Baltimore Avenue at 7th Street, you’ll see a street lined with charming older homes, many of which are available for rent.