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The perfect spot for your next weekend getaway, I was lucky enough to call this amazing place home for a few years

When I was growing up my family often took weekend trips to the beaches in Delaware and Maryland every summer. The trip home usually included a stop in Annapolis. My dad liked going into a camping store in the mall and my aunt, who didn't live too far away, would meet us at a Chinese restaurant there that she frequented. On one particular trip I remember my aunt taking my cousin and I downtown. Main Street was absolutely charming with its brick street, local shops, and restaurants. From there we made our way to the docks and hopped on a ferry that went out into the bay and stopped under the Chesapeake Bay Bridge before turning back. It was beautiful, and I remember thinking how cool it would be to live there.

I made it back to Annapolis quite a few years later, in 2007, for a team building event we had planned at my place of employment. We chartered one of the Schooner Woodwind sailboats that took us out in the Chesapeake Bay and then over to Cantler's Riverside Inn for a feast of Maryland blue crabs, corn on the cob, and cold beer. I would highly recommend doing a private charter or one of the scheduled public tours they offer. Fun Fact: One of their sailboats was used in the movie Wedding Crashers, they had a book on-board with photos of the cast and crew.

Fast-forward to 2015 when I actually bought a house and moved to Annapolis! I found a cute craftsman house on the Eastport side of Annapolis in a neighborhood called Timber Creek. If you're ever looking to move to Annapolis check the neighborhood out. It's a quiet, with rustic charm, tucked away from the busy streets with some very tall trees. While it was the perfect spot to settle down for a minute, after a few years was time for another change. So what better way to say goodbye to this beautiful place, a little over a year late), than to highlight some of my favorites places and events?

NOTE: Obviously with COVID the menu items and events may be a little different for a while, but these are my suggestions for when everything gets back to normal, or closer to normal...



Located in the heart of downtown Annapolis with large windows that open up to Main Street when the weather is warm, Preserve was named one of Washingtonian Magazine's Top 100 Restaurants of 2018. The menu is sustainable and sourced locally, and every dish includes a pickled, preserved, or fermented element. Some dishes seem to remain on the menu year-round, while others change with the seasons. I've never had bad food here but I do have some favorites.

  • Kale Salad - The combination of fried kale, served with pickled red onion, cumin yogurt, and a red pepper jelly is a delicious combination. It's a large portion, perfect for the whole table to share!

  • Pierogis - The flavors usually change but this is often a staple on the menu and rightfully so. If a place has pierogis on the menu I'm probably going to order them.

  • Pickled Appetizer - Featuring an array of picked vegetables like cauliflower, onion, carrots, celery, cucumber, peppers, and radishes, this is a must get dish if you're a fan of pickled anything. My favorite was the daikon radish!


I so wish I had some pictures of the food here, but they're usually too dark or I'm not in the right state to take good pictures. Located on West Street in what's considered to be part of the Annapolis Arts District, this sushi / Asian fusion restaurant features a beautiful mural on the the face of the building, which actually generated a lot of controversy a few years back. They also feature regional artists on the walls of the restaurant (side note: the artists sometimes frequent the restaurant so if you don't like something, it's best to keep that to yourself, one of my friends learned that lesson the hard way). My favorite things here are the cocktails - super creative and always delicious, and all of the sushi - especially the garden roll that comes drizzled with a delicious scallion vinaigrette dressing.


Southern inspired cooking at its finest! Located in a great spot with views of Ego Alley, there are so many "must try" dishes on the menu. I've only ever been here for breakfast, and they do not take breakfast reservations so there is usually a wait, but worth it, and if it's long enough you an stroll around downtown. Some of my favorite things here:

  • Bacon Bloody Mary - Really good base flavor with just enough heat, a giant piece of bacon, and pickled asparagus that I could eat all day long

  • Roostarts - One of the things I miss most about Annapolis, these homemade "pop tarts" are ridiculously good. With flavors that change every day I think my favorite so far has been the Reese's Pieces version. Much to my delight they've started shipping these beauties around the US so you can make them at home!

  • Rancher's Benny - A vegetarian benedict packed with flavor, from the fried green tomatoes to the roasted poblano sauce, hollandaise, and corn salsa, this dish is amazing from first to last bite


  • Lemongrass - The red Thai curry here is amazing

  • Vida Taco Bar - Delicious margaritas made with nothing but fresh ingredients

  • Eastport Kitchen - Avocado toast for breakfast or the grilled cheese for lunch

  • Fox's Den - So many good pizzas

  • Potato Valley - Baked potato bar open for lunch

  • Boathouse - Crabcakes to eat and orange / grapefruit crushes to drink

  • Cantler's Riverside Inn - Crab dip with tater tots and literally any of the fresh seafood, but mostly the crabs (and it's not technically in Annapolis, but close enough)

  • Level - A small plates lounge with delicious bites and try the Angels and Demons cocktail, the habanero is not aggressive and the micro cilantro gives it such a good flavor

  • Dry 85 - A modern industrial style take on a Prohibition-era speakeasy, the liquor selection here is ridiculous and they make some of the best cocktails I've ever had, and the truffle fries are a great snack



In what can best be described as 'The Great Gatsby' meets traditional Annapolitan style, the Annapolis Cup is a croquet match held every Spring between St. John's College and the U.S. Naval Academy. Attendees are entertained by the match while drinking wine, champagne or beer on the lawn of St. John's. It's truly a fun event just for the people / outfit / hat watching alone. Here I am attending the event in 2017. You must have tickets to get into the event and they do sell out rather quickly, so if it's one you want to attend keep an eye out of the St. John's website for ticket sales and information.


A years-long tradition every fall, a rope is stretched across the water from Eastport to Annapolis and various teams compete in matches. It's actually the longest International Tug of War over the water in the world. With a lot of the money raised going to charity, it's a great way to give back and have a lot of fun at the same time. If you're going to check it out, the Eastport side is a lot more fun. There's beer, food, and music and while the tugging only lasts for a couple of hours, the party goes from 10-5 usually.


A local music festival usually featuring 4 stages and countless bands. The festival started in 1998 and showcases up and coming local bands with a wide range of styles, along with some long-time local favorites. Some recognizable bands to come through this event have included Good Charlotte and Jimmie's Chicken Shack. The food selections include BBQ, local seafood, shaved ice, and more as well as a wide variety of domestic and craft beers and cocktails. For those with kiddos you'll find face painters, tattoo artists, moon bounces, and other family friendly activities. Proceed from this event also go to local charities.


Organized by The Eastport Yacht Club on the second Saturday in December every year, this festive parade features boats decorated in a ton of Christmas light-glory making their way through the Annapolis Harbor to the delight of onlookers. My favorite that I remember featured a giant leg lamp from A Christmas Story, but there are always amazing light creations to behold. You can find spots to watch from the Eastport Bridge, Naval Academy, City Dock, Ego Alley, or there are some others if you know anyone who might have a home or office or even a boat along the harbor area. Make sure to dress warmly, it can get pretty cold watching from the waterfront!


  • There are lots of great little shops downtown on Main Street and Maryland Avenue to check out on a nice day, or even before Christmas when they do Midnight Madness

  • Do anything on the water - boating, fishing, paddle boarding

  • Tour the Maryland State House, lots of cool history here

  • Check out the concert schedule at Ram's Head On Stage, some really good names come through there



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