After leaving Oxford at 9:30 a.m., we made a leisurely run up to St. Michaels, MD. for an overnight, arriving around 1:20 p.m. We had been there 14 years ago aboard our first Misty with Justin and Bryan, and loved it. St. Michaels was an early shipbuilding center, where the swift Baltimore Clippers were built. Now, St. Michaels is a packing house center for seafood and tomatoes, as well as being home to many working fisherman. The small harbor on the Miles River is beautiful, and the charming town wraps itself around it. The restored Hooper Strait Lighthouse at the Chesapeake Bay Maritime Museum greets you as you approach the center of the harbor.
The Museum is well worth exploring, sitting on 18 acres on the harbor front with an extensive collection of historic bay boats and a detailed look at the areas maritime life.
The entry to the Maritime Museum
Since the weather wasn’t great, and we had explored the Chesapeake Bay Maritime Museum during our last visit, we decided to skip the museum this trip, and just wander around town exploring the shops and beautiful streets of St. Michaels. St. Michaels has grown! There are lots of cute shops and places to eat and of course, Justine’s for ice cream
Scenes around St. Michael’s
It was Mother’s Day, so we had dinner out, catering to Nancy’s yearning to have a bucket of crabs dropped on the table.
Mother’s Day dinner!
We enjoyed our meal at St. Michaels Crab and Steakhouse, and can also recommend the Crab Claw across the harbor, a short walk through town.
And, in case you can’t find a restaurant serving crabs, you can follow the painted signs on the sidewalk!
A bit further out of town, on the other side of the Maritime Museum is The Inn at Perry Cabin. The restaurant there is wonderful, but definitely a special occasion kind of place.
The Inn at Perry Cabin
We stayed at St. Michaels Marina, which is lovely, and the staff is great, but it’s expensive and charge a whopping $20.00 for a pump out! Sailors beware!
Misty at St. Michael’s Marina
We were thrilled to meet Jim and Beth Gausman, fellow “Loopers” aboard Inuksuk a 40′ Mainship (that’s their boat to the right above, Misty’s on the left). We ended up bumping into them in Annapolis and Croton-on Hudson (below), and had a great time getting to know them.
Jim and Beth aboard Inuksuk
Annapolis was a short 3 hour run across the Chesapeake from St. Michaels. We left St. Michaels Marina around 9:30 am in overcast weather in the 60’s with a little fog.
It cleared a bit as we crossed and we saw a number of freighters anchored in the bay, waiting to head into port up in Baltimore.
Views on the water
The iconic Thomas Shoal Lighthouse sits majestically closer to the western shore of the Chesapeake as you near the Severn River.
Thomas Shoal Lighthouse
As you enter Spa Creek, you’re greeted by the beautiful U.S. Naval Academy.
U.S. Naval Academy
We highly recommend taking a tour of the Academy, and, during the school year you can watch the noon formation in front of Bancroft Hall. This is the beautiful Beaux-Arts building that is the largest single dormitory in the world.
The campus itself is beautiful, sitting on the edge of the harbor:
Scenes around the U.S. Naval Academy
The Chapel on campus is spectacular, and houses the Tomb of John Paul Jones. It’s extremely ornate, reminding us a bit of Napoleon’s Tomb in Paris!
John Paul Jones’ Tomb
Main Street is loaded with great shops and places to eat. Chick and Ruth’s Delly , also known just as Chick n’ Ruth’s, is a must! It’s a kitchy diner style restaurant, that has remained unchanged since it opened 52 years ago. This is an extremely popular place, known for its corned beef, crab cakes, homemade pies, milkshakes and breakfast all day. Every weekday morning at 8:30 am (9:30 am on weekends), patrons rise and recite the Pledge of Allegiance, led by an employee over a microphone, facing one of the many flags hanging around the restaurant. This has been a Chick & Ruth’s tradition since 1989.
A visit to the Maryland State House at the top of the hill in town is a must. It is the oldest state capitol in continuous legislative use, and is the only state house ever to have served as the nation’s capitol. This is where George Washington came before Congress to resign his commission as commander-in-chief of the Continental Army and where the Treaty of Paris was ratified, marking the official end to the Revolutionary War.
Maryland State House
There are several options for tours around town, either walking or by electric vehicle. We opted for a 1.5 hour tour in an electric vehicle that was great. There are also several beautifully restored houses to explore throughout town: Paca House and Garden, Hammond-Harwood House and the Chase-Lloyd House are a few we toured.
The food in Annapolis is great! During this visit we had an amazing seafood meal at The Boatyard Bar & Grill. Everything is fresh and delicious, but the crab cakes are particularly amazing!
The fabulous Boatyard Bar & Grill
The perfect end to a wonderful meal? A slice of Smith Island cake, sent over via ferry from the island further south in the Chesapeake!
Smith Island Cake
Pusser’s is a great spot for a drink and watching the boats on Ego Alley. O’Leary’s in Eastport (just across the Creek) is also known for their crabcakes, and Harry Brown’s near the State House is another excellent choice. These two are a bit pricier, but worth it. For breakfast, don’t miss The Iron Rooster, right downtown across from Ego Alley and Mason’s Lobster Rolls on Main Street is good for a quick and delicious lunch.
The Annapolis Yacht Basin is ideally located adjacent to Ego Alley, with a great staff, clean laundry facilities and gorgeous bathrooms. We’ve stayed there twice and will certainly go back to one of our favorite places on the Chesapeake.
Annapolis is one of our favorite spots on all of the Chesapeake. We have been twice by boat now, and each visit lasted 3 – 4 days. There is never a shortage of things to do, wonderful shops to explore and neighborhoods to wander through and great places to eat! When we return in the fall, we plan to check out the mooring balls out in the harbor for a change of pace. It should be fun to scoot in and out of Ego Alley on our dinghy!
Beautiful Annapolis Harbor