My friend, Maribeth, and I signed up to run the Wayfarer’s Inaugural Half Marathon Saturday, June 2nd, 2018, and decided to make a weekend of the charming cobblestone streets lining the Chesapeake Bay in Annapolis, Maryland!


We originally signed up for the Half Marathon, but received notice on Friday that we had been downgraded to the 10K due to bad weather coming in.  The course began at the Navy Marine-Corps Memorial Stadium and winded through scenic historic Annapolis, ending back at the Stadium.   My favorite part was being able to go inside the stadium – it’s beautiful!!! Overall it was a great race, and one I would do again if in the area.


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Waiting on us at the finish line was the best Post Race Party ever featuring a complimentary beverage from Jailbreak Brewing Company and our choice of donuts from Glazey Days Donuts, Pizza from Dizzy Cow Pizzeria, or Crab from Crab Town Curbs!  Of course we chose Beer and Donuts, and they were both GREAT!



Wayfarer’s official lodging partner was at the Lowes Annapolis, however, it was booked, so we stayed right next door at the Hilton Garden Inn Downtown Annapolis.  It was within easy walking distance of the race, Main Street, the United States Naval Academy, and everything else historic downtown Annapolis has to offer.  Loved the hotel, with the exception of the HORRIBLE customer service provided at checkout.  I will be calling the manager to discuss!


I had texted my good friend Scott, who is a Naval Academy Grad, and asked him for ideas on where and what to explore, eat, drink, etc.  He gave me a whole list of places to go.  After we checked in to the hotel, we decided to try Scott’s first recommendation – Ram’s Head Tavern for dinner and a cold beer.  Once in the basement of this 250 years old pub you know you are in a historic building when the walls are bare red brick.  We started with the Ram’s Head IPA and Crabby Tots – tater tots topped with crab dip, cheese and Old Bay seasoning.  I ordered the Shepard’s Pie and Maribeth chose the Blackened Tuna – It was a good dinner, and a nice atmosphere, but not OH MY GOD SO GOOD – YOU MUST TRY.  



We had reservations to visit a winery at 1:15, so after the race we decided to walk around downtown, visit the Midshipmen’s Store at the Naval Academy, and grab lunch before heading to the winery. 

But first – Coffee!  You all know my love for trying new coffee shops so I had to try the one my friend recommended – 49 West Coffeehouse.  Sorry Scott, not impressed, while the shop is known as “Annapolis’ Living Room,” the coffee was not good! 

While you may know Annapolis as Maryland’s state capital, did you know that it was also the capital of the United States for a brief time in 1783?  There is so much history here!  Right down the street from our Hotel, just before you hit Church Circle, lies the Maryland Inn. This hotel dates back to 1772, and is the oldest continuously operated hotel in the country.

Maryland Inn

Maribeth said, “Let’s go in and just look.”  However, you cannot walk in, you have to be a guest and you have to check in at a different building to obtain your key.  We took the stairs on the outside that led to the cellar where there is a coffee shop.  On the inside the walls are stone and exposed brick, it’s a warm and inviting place with comfortable chairs, a leather couch and lots of historical memorabilia adorning the walls indicating that it used to be a jazz club.  The most intriguing thing to me was the TUNNEL hidden in the far corner to the right where wrought iron bars block the entrance.  


Another one of Scott’s many suggestions was Mill’s Fine Wine and Spirts owned and operated by two of his classmates from the Academy.  We popped our heads in to say hello to Jen and let her know that Scott said hello.  We got lucky as they were holding a beer tasting from Antietam Brewing.  I tried the Little Mac IPA – A classic, crisp American style IPA brewed with fresh grapefruit and five hop varieties from the Pacific NW and 10% malted rye. Very hop forward and very delicious!  I usually only try IPAs but he had a beer that was purplish in color and supposedly tasted like raspberry so I had to try it!  It was Otto’s Orchard Series – A hearty wheat beer base complimented by seasonal fruit purees. Varieties include, raspberry, blueberry, boysenberry, and tart cherry.  Very Good!!! If you are ever in Annapolis and need some adult beverages, go to Mill’s and see Jen and Jerry, they have you covered with over 100 beers available and free beer and wine tastings every Friday and Saturday.  If you find yourself in or around Hagerstown, Maryland, go check out Antietam Brewery, western Maryland’s first craft brewery. 

Shopping in Annapolis (if you want to shop small) is best on Main Street, Maryland Avenue, and Annapolis Street, though there are also a few boutiques on State Circle, West Street, in Eastport, and sprinkled throughout the rest of the city.  We walked into several on our stroll, but my favorite find was Sea Bags!  My friend Melissa turned me on to these totes made out of real sails and I have been following them on the gram for quite some time. I own one bag and I bought one for Melissa as a gift.  Sea Bags are nautical-themed totes made out of recycled boat sails on the working waterfront in Portland, Maine.  I had no idea that there was a location right there in Annapolis!! I was so excited when I saw the store front, it looked just like the pictures I had seen so many times on Instagram – I HAD to go in! 


A boater had just dropped off a Sail before we went in, it was still lying on the floor.  Through their Sail Trade Program, they offer Sea Bags in trade to their customers.  Owning a Sea Bag is like carrying a story on your shoulder and these stories start with the Sailors who bring in the sails.  No, Jerry, I did not buy a new bag – I only looked! 


There is no denying the U.S. Naval Academy is the anchor of downtown Annapolis.  I have been here several times, but Maribeth had not been.  On Saturday we only went to visit the Midshipmen’s Store and we planned on getting up early Sunday morning to go run around the campus so I could show her all the beautiful architecture and history it has to offer (however, it rained and we did not make it).  No matter how many times I go, I cannot help but get caught up in the sense of pride and awe as I step on the grounds of the U.S. Naval Academy. One of these days I want to take a guided tour so that I can learn more about it and make my experience more meaningful!

My run around the Academy on my last visit in May 2017


We only had one hour before our wine tour began so we decided to grab lunch at the popular Boatyard Bar & Grill.  I had done tons of research online and this seemed to be the most recommended for seafood.  It is located on Restaurant Row in the historic maritime district of Eastport.  The interior is like that of an old yacht, with shiny white walls, mahogany, sea foam green ceilings and large wooden beams. There are many paintings and items collected during the owners’ travels – The old wooden fishing skiff that was bought off a beach in Saint Barths, an original wooden sign from Hogs Breath Bar in Key West, and a surfboard autographed to the Boatyard by singer/songwriter Jack Johnson are just a few that I remembered seeing.  


We only had one hour, and of course it was packed, so we grabbed a seat at the bar.  I ordered the Lobster Roll and Maribeth got Blackened Tuna AGAIN.  The food was good, but nothing to write home about – especially since I have had fresh lobster right out of the waters of Maine.  It was a great atmosphere with excellent and fast customer service!  Baltimore Magazine named their crab cakes on its list of Best in the Region and was the only Annapolis restaurant on the list.  The article states that “the Eastport neighborhood gathering spot feels like a congenial yacht club in a preppy New England village.  Two broiled cakes, crisp around the edges…are low on filler and seasoned with an old bay bite…washed down with a local draft…there’s nothing better after an afternoon on the water”.  I will definitely go back just to order the crab cakes!



Great Frogs Winery is located just minutes from downtown, however it feels like it is worlds away in another country.  When you turn into the driveway, you will see a rustic farmhouse nestled back behind the vineyards. 


This was definitely the highlight of my weekend, it was so worth stepping away from downtown for a bit.  The tasting room is behind the barn, it is the newest addition to the property and it is so beautiful! The tastings are by appointment only on Fridays and Saturdays, once we arrived they sat us at our table and brought all of our tastings to us at one time so that we could take our time and taste at our own pace. 


Their wines are mostly dry, however, they did have one sweet wine that they pulled out and let us taste!  Out of the dry wines, I liked the 2016 Tanyard the best.  The sweet wine is named Lollipop Red – it is delicious!  I brought a bottle home with me and I am enjoying a glass right now with my frozen pizza and salted caramel fudge as I type this blog post! 


After our tasting we wondered around the property taking pictures and ended up in the rustic barn which was once a tobacco barn  that dates back to 1691.  Here we enjoyed some live music until we decided to leave. Be sure to add this place to your list if you are in Annapolis – it is a must, even if it’s just to enjoy the scenery!



Known as the “Sailing Capital of the US,” Jerry and I took a Sailing cruise with Schooner Woodwind Annapolis Sailing Cruises on our last visit to Annapolis.  

From May 2017

With over 533 miles of shoreline and the Chesapeake Bay as its backyard, there is no better way to experience Annapolis than out on the water.  Maribeth wanted to do the sailing cruise so bad, but the weather was just awful so we opted for a movie instead – Adrift.  If you have not seen this harrowing, heartbreaking real-life story about Tami Oldham Ashcraft’s 41 days stranded at sea, you must go!  


After the movie we walked around downtown some more and then decided on dinner at the Iron Rooster.  On my last trip, Jerry and I ate breakfast here and I loved it!  Whether you are looking for breakfast all day, lunch, supper or drinks, Iron Rooster specializes in comfort food, hospitality and community!  Pro Tip:  Try the Housemade Roostart (poptart), they are made fresh daily – ask the server for their current flavors.

  Iron Rooster

I was looking forward to exploring the supper menu and wanted Maribeth to experience the place as well.  I decided to order the Cakes on Cakes – house made crab cakes on top of cornmeal cakes with fried green tomatoes, chipotle hollandaise, asparagus and corn salsa with old bay seasoning.  Maribeth ordered what they are famous for – Chicken and Waffles – buttermilk marinated fried chicken breast on tope of cornmeal waffles covered in black pepper pan gravy.  The food was good, and the hospitality was great as promised!

There are several ice cream shops lining the brick paved Main Street, but my research showed that Annapolis Ice Cream Company (no website available) was the “must try.”  It has won the “Best Ice Cream in Annapolis” for the past 10 years.  They have all the classics, but also make very creative flavors – I tried the Oreo Peanut Butter and Maribeth had just plain Oreo.  We both loved the ice cream – but were also very full from eating all day!  Will definitely go back to explore more flavors on my next trip!  


One of the first things Scott stated when he texted me his recommendations was “Amazing Brunch at Miss Shirley’s.”  One of Maribeth’s coworkers suggested it too, and of course all the research online states that it’s a must!  So, Maribeth and I made plans to get up early and be the first ones in line for Sunday breakfast so that I could get on the road back to Norfolk.  This place was AWESOME!!! Let me start with the coffee – they serve Rise Up Coffee which I had read about online and it was SO GOOD!!! It seemed that a lot of places in Annapolis served this coffee, but Rise Up itself only has two locations and they were not nearby.  

Now, for the food – Maribeth ordered the Mexican Street Corn Fried Deviled Eggs as an appetizer.  I DO NOT like deviled eggs, so I did not plan on trying them!  BUT, let me just say, they are DELISH – breaded in Panko and fried, filled with Queso Fresco, Roasted Corn & Cilantro, topped with Red Onion, Queso Fresco & Crispy Corn Tortilla Strips, garnished with Comeback Sauce and dusted with Smoked Paprika.  There were so many things on the menu that I wanted to try, for example, they have Funky Monkey Bread – Cinnamon-Scented Pull-Apart with Banana Slices, Chocolate Chips & Chocolate Sauce, dusted with Powdered Sugar & Cinnamon.  However, b/c I had been eating ALL WEEKEND I decided to get something on the healthier side – 2 Farm Fresh Eggs, Cranberry Maple Turkey Sausage, Shredded Potato & Onion Hash Browns served with a House-Made Biscuit.  The waitress said, “would you like anything sweet?” I was like Yes, I do, do you have any half-size orders?  They did, so I ordered the Belgian Waffles – 2 little mini versions.  All of my food was delicious!  Maribeth ordered the Soft Shell Crab & Succotash Eggs Benedict – Cornmeal – Encrusted Soft Shell Crab, Chesapeake Chicken Sausage, Black-eyed Pea Succotash & Poached Eggs on a Jumbo English Muffin with Old Bay Hollandaise, Tabasco Bacon Onion Jam, Chow Chow & Comeback Sauce dusted w/ Old Bay.  When it came out it was literally a whole crab just deep fried.  I had made this mistake last year on a trip to Maryland with Jerry – I knew I did not want anything that had “Soft Shell Crab” in the description, I just assumed Maribeth knew what she was getting herself into.  


OMG, her face – I’m literally dying laughing as I’m typing this just thinking about how confused she was!!! She started screaming “Help” “Ummmm, please Help Me!” 


When the waitress came over she asked “How am I supposed to eat this?” She responded, “You just eat the whole thing.  You must not be from here?”  Maribeth smiled, and said no, but thanked her for helping.  She moved the crab and ate everything else!  Overall our experience at Miss Shirley’s was good and I would definitely say that it is a MUST TRY!!!

Annapolis has so much to offer and I cannot wait to go back again!  Attending a Navy Football game is definitely on my Bucket List!


I wanted to try another coffee shop, so I did some research and found one that looked good in Alexandria, VA – Swings Coffee.  SO GOOD – They know how to make a great Vanilla Latte!!!!  I will definitely go back when I am in the area.


While researching coffee shops I found an article about the narrowest house in America – so you know I had to do a drive by!


See that tiny blue house wedged in between the white and red ones? It was built in 1830 and is only 7 feet wide. The Spite House, as it’s called, has two stories but only 325 square feet. It even appears to be considerably shorter than its neighbors.  Click here to look inside!

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