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Wednesday, June 1, 2022

Weekender's Guide to: Northern Chesapeake Bay, Maryland

Today's Weekender's Guide was a chance to visit Maryland and a trial run of sorts. We are going to Portugal next month and traveling abroad with a 15-month-old (his first flight will be nearly 7 hours) was giving me a boatload of anxiety. Whitney is in that age range where traveling with him is a complete wild card. He is on the move, full of attitude, and on a schedule. Gone are the sleepy, immobile days of traveling.  

I was especially terrified of "naps on the go" as we can't rush back to the Airbnb for 2-3 hours every day while we are out traveling. We traveled a fair amount his first year but he has changed a lot since some of our last trips. I needed the confidence to travel with a toddler out of his element and routine. He is an amazing sleeper at home but he is conditioned to that dark quiet room and his crib in his room. I really needed him to be able to nap in his stroller or in the car on the go. More importantly, I needed to prove to myself that I could do it.

Downtown St Michaels, Maryland

For our "trial run" and weekend getaway, we decided on a road trip to the Northeastern Chesapeake Bay of Maryland. I had never been to the state (besides driving through) and I was excited about spending time on the water with Adam and Whitney to kick off the summer. I'll share a separate guide on a few things that really helped us road trip with a toddler (through temperatures ranging from 60s to 90s). But this is a travel guide. This is a Weekender's Guide, the things worth seeing, the food worth eating, and a few things in-between. It focuses on the northern/central portions of the pay, visiting Chesapeake City, St Michaels, Easton, and Annapolis. 

Friday: Drive to Maryland - stop in Chesapeake City for lunch/dinner. Head to the hotel in St. Michaels. 
Saturday: Spend the morning in St. Michaels. Head to Annapolis (walk around the city, eat, and take a tour of the Naval Academy). Spend the rest of the day/evening in the city 
Sunday: Spend the day in St. Michaels (maritime museum, shops, parks, boat ride). Have lunch and pack up. Stop in Easton on your way out. Have dinner and walk around the town. Head home. 

Chesapeake City 

Dinner on the docks 

Chesapeake City is currently the only town in Maryland that is situated on a working commercial canal (and one of the busiest in the world). It's a cute little town on the water and it's the perfect spot to stop for a drink or lunch while driving through (here's a dining and nightlife guide). If you have extra time, it's known for its bed and breakfast spots. For us, it was the perfect stop at the top of the bay with a fussy kid on our road trip to St. Michaels. While walking around, we noticed the very busy Tikki Bar on the docks at Schaefer's Canal House. It was a bit too busy for us so instead, we went to The Rummer Lounge, the outdoor rum garden at the Inn at the Canal. We sat on the Adirondack chairs on the lawn and let Whitney play while I drank a beer and Adam and I split an order of tacos. 

St Michaels

Park in St Michaels, Maryland

St Michaels is a quaint downtown area with shops, restaurants, a museum, parks, and a brewery. Our hotel was in St Michaels and it was going to be our home base for the weekend. It is a popular picturesque harbor on Maryland's Eastern Shore. It became famous as the backdrop for the movie Wedding Crashers and was named as one of the Top 10 Best Small Coastal Towns in America by USA Today.  Its harbor and some homes date back to the mid-1600s and is home to the Chesapeake Bay Maritime Museum. The main street is full of interesting shops and restaurants and it's a great place to spend the weekend. We also loved the cute little parks in town and we were pleasantly surprised with the food. We found the Main Street to be a bit busier with car traffic than we expected and our bikes never made it off the car rack. We grabbed coffees at the cute little coffee shop, Blue Heron Coffee (a micro-roaster that brews its own coffee), had savory and sweet crepes at Crepes by the Bay, and had dinner at The Crab Claw (touristy and pricey but its location on the docks and seafood menu made it work it), had another great dinner at Awful Arthurs (a great dinner at a fair price), and spent a quiet morning at the Chesapeake Bay Maritime Museum (a great museum with a lot of outdoor exhibits spread out through the waterfront, great for kids to explore and history buffs to enjoy - definitely make a stop). There are also boat cruises, a brewery, a winery, and a lot of shops to check out while you are in town. It's a great weekend town to take in some of Maryland's history.

Dinner at The Crab Claw, St Michaels

The Crab Claw, St Michaels

Crepes by the Bay, St Michaels

Chesapeake Bay Maritime Museum, St Michaels

Chesapeake Bay Maritime Museum, St Michaels


Naval Academy, Annapolis, Maryland

Annapolis was a 1-hour drive over the bridge, across the bay, and over to the other side of the Chesapeake Bay. It's the Capital of Maryland and home to the United States Naval Academy. We were there during "family weekend" and we were greeted by a busy scene and a lot of students in their uniforms. We were charmed by how cute the city was and truth be told, I had one of the best lobster rolls (ever) downtown at Mason's Lobster Roll. It's known as the sailing capital of the US and the city has some pretty fun (and funny events). If you visit in March, you can take part in the "Annapolis Oyster Roast & Sock Burning", a tradition each March 21 since 1978 when guests come out of hibernation to burn their old winter socks and ceremoniously welcome spring with live music, oysters and libations. We stopped at the Naval Academy and loved walking around the beautiful grounds. One of our favorite aspects of the trip was enjoying the waterfront on a shaded pair of Adirondack chairs on a hot humid day (your expectations really change when traveling with kids). You can also take a tour of the academy and stop in the Visitor's Center Gift Shop (you will need an I.D. and to go through a metal detector to enter the academy grounds). 


On our way out of St Michaels, we stopped in Easton to check out the downtown area. Easton has been voted  “the 8th Best Small Town in America” and has also been called the "Hamptons of the Chesapeake Bay". We walked around the downtown area and wandered through a cute little park before finding a spot for lunch. We wandered into Doc's Downtown Grille, lured in by their awesome outdoor patio. We loved the fantastic menu and everything we had was so so good. It definitely seems like the more residential town in the area and it's also where you can find your bigger retail stores. 

The Downfalls/Skippables

If you look at the map of the area, you will expect to see sweeping waterfront views everywhere you go. This is not the case. A lot of the land along the waterfront is private land and farmland so expect to see waterfront views only at public parks, marinas and restaurants. We were also bummed that we never really found a place to ride as there were no great designated bike lanes and there was more traffic than we were comfortable with. We also made the trek out to Tilghman Island, expecting a cute little town and awesome views and didn't really get either (don't waste the gas). If you have a boat or want to rent a boat, this is a great place to explore. I also highly reccomend heading out on a kayak or SUP. We had a toddler with us which limited our on-the-water excursions. Without a boat, there wasn't much to do besides shop/eat/wander. You won't find any beaches or places to swim and I read that the jelly fish get so bad you wouldn't want to either. That being said, we enjoyed a nice little weekend away and the travel practice with Whitney before a bigger trip. While we had a great time, it wasn't somewhere we felt the need to go back to (with the exception of Annapolis, I would go back in a heartbeat) and would love to explore the southern area of the bay and the ocean side of Maryland on our next visit to the state. 

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