Taverns, or ordinaries, were one of the pillars of life in the colonial villages that dotted the Chesapeake Bay shoreline in the early days of our country. These establishments were woven into the very fabric of a community’s economic, political, and social activity. Typically situated at busy crossroads, ordinaries served both locals and travelers. The tavern owner also often functioned as postmaster, real estate agent, auctioneer, arbitrator, and referee.

The Maryland colony began licensing ordinaries in 1658, but there were any number of taverns and ordinaries operating around the Eastern Shore by this time. In fact, it’s likely the first tavern in what would become the state of Maryland was located in the long-gone bay-side village of Broad Creek on Kent Island, dating back to the 1630’s or 1640’s.

The Chesapeake region was known for its home-cooking and hospitality for generations, up to and through the Civil War Era. In the days of the grand bay resorts and in-town boarding houses, few guests ever complained about an Eastern Shore meal. After the Bay Bridge was completed in 1952, there was an explosion of roadside dining options available to the modern gourmand on the go.

In the 1960’s and 1970’s, the following were some of the local restaurants serving the Gateway to the Land of Pleasant Living:

The first stop after crossing the Bay Bridge would have been Pier#1 Marina & Restaurant, now and for many years known as Hemingway’s.Scan0001This Bay Times ad suggest the restaurant was newly opened in March, 1971. In my opinion, Hemingway’s still has the best view on the Chesapeake Bay.14053681_1096829447059778_1848269031856176769_o

14124272_1096830200393036_1273467414370434734_ocourtesy: http://hemingwaysbaybridge.com/

unnamed (1)Joe Downey’s Tastee Freeze was a drive-in on the corner of Routes 50/301 and Cox Neck Road that served soft ice cream, hot dogs, hamburgers, and excellent fried chicken. For a Queen Anne’s County teenager in the 1960’s and 70’s, ‘breezing the Freeze’ with friends or having a first-date Tastee milkshake  was a rite of passage.


Dezes Inn was a popular fancy restaurant in the era of my youth, serving elegant dishes well beyond the simple pan-fried softcrab and homegrown tomato on white-bread sandwiches, field picked corn-on-the-cob and watermelon, and 3-layer chocolate Granny cakes that we were used to down our way.


I guess, one man’s delicacy is another kid’s whole summer menu.Scan0006

Once known as the Shamrock Inn, owned by Anna Haspert, and then her daughter Kate Barton, and before the Deze family took over,  Mr. Bill Ripple and his wife ran the Old Cove Inn there for a few years. The Old Cove was later renamed Bootlegger’s in honor of the location’s one-time notorious reputation. Though there is still a Shamrock Street, near Adam’s Ribs, 5 Guys, and the new IHOP,  the giant old building that had served thousands of customers over the decades has been lost to history for many years now. I tended bar there for a short time in the 80’s during a disastrous fly-by-night operation known as O.O. Forbes.

The upstairs had hidden passages, and the whole joint was believed to be seriously haunted. I never saw dead people.

Just drunk people.



One of my first jobs was working as a busboy at Chesapeake Restaurant in Grasonville. Different owners have come and gone since, for a while the very popular Chesapeake Chicken was located there, but in recent years an antiques mall called Shipwrecked called the old building home. It, along with the 50’s-era row of hotel rooms that was part of the property,  was recently razed to make room for a new WaWa convenience store.Chesapeake Motel and Restaurant Grasonville, MD

The back of this postcard courtesy of https://www.cardcow.com/ reads:

Serving Shore’s Finest Seafood, Steaks and Chops U.S.Highways 301 and 50, Grasonville, Maryland – Phone TAylor 7-7272 7 Miles East of Chesapeake Bay Bridge Modern Air-Conditioned Units in a Tranquil Country Atmosphere. Wall-to-Wall Carpeting – Artesian Well Water – Free Television. Owned and Operated by Mr. & Mrs. James A. Miliner and Son

A few other area eateries of the 60’s and 70’s include:Scan0005The Poseidon Inn was a popular restaurant and nightclub on Kent Narrows north where Annie’s Paramount Steak and Seafood House is now, near Harris Crab House and Seafood Restaurant and Red Eye’s Dock Bar. Portside is now The Jetty on the southeast side, near Bridges Restaurant, the enduring Fisherman’s Inn & Crab Deck, The upscale Narrows, and Big Owl’sEbb Tide Restaurant was originally located over the Kent Narrows Bridge in Grasonville, but later moved to a Kent Island location.  For a couple generations, Ebb Tide was THE place to go for local seafood and the four dollar crab feast. Scan0002


All ads courtesy of the Bay Times newspaper collection.

Ebb Tide:10-2-3courtesy: Kevin George







19 thoughts on “A HERITAGE OF HOSPITALITY – THE 1960’S AND 70’S

  1. My sister and I were talking about the old restaurants that used to be on the island years ago. Thanks so much for posting this. I really enjoy your articles!

  2. Wonderful article. Brought back so many great memories from when dad started his practice. Walking down to the Bay Bridge Motel and Resturant. And on weekdays when the traffic wasn’t bad, walking across 50 to Ebb Ride and Stuckys. Great times thanks Brent

  3. wow, nice to reminisce those days…Especially I used to love EBB tide too when it was in Grasonville..and Chesapeake Resturant, I remember working there when I was about 18 19 years old..they called it Queen Anne Inn then..That first restaurant “The four seasons”, I cant seem to recall..where exactly was that Brent?

  4. Thanks for posting Brent. I went to all of these including a wedding reception at the Chesapeake Restaurant. Played on the Ebb Tide softball team a season or two so lots of post-game celebrations or commiserations. I am not sure when the Tastee Freez was taken over by Joe Downey or who had it originally but I think for part of the 60s Buddy Sparks had it.

  5. Sure brings back memories. We lived in Grasonville until we bought our home in Castle Marina. Lived there for 9 years. Loved every minute of it.

  6. There was a Restaurant – Motel called the “Islander” right after the bridge that my Dad always stopped at for breakfast when we were going to OC. They had the BEST Pancakes I’ve ever had in my life! Anybody remember it?

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