- Date of Visit: July 4, 2021
- Weather: Sunny, with pockets of clouds, hot but not humid, temps in the upper 70’s
- Music: First Sunday Arts Festival musicians
Annapolis is one of the main tourist attractions and school field trip destinations within the state of Maryland. You would be hard-pressed to find a Maryland resident who hasn’t taken a school field trip to the State House or the Naval Academy, or a tourist who hasn’t seen the City Docks, or the tall ships on the Severn River and strolled along the old historic streets. Visiting Annapolis is almost like stepping back in time: many of the buildings, which now house sushi restaurants, Starbucks, comic shops, or even a spice store, date back to the colonial, Georgian, and Federal periods. Annapolis was founded in 1649 by Puritan settlers, and in 1695 became the colonial capital after it was moved from St. Mary’s City, and named Annapolis in honor of Princess Anne Stuart. [1]
While Annapolis’s population is too large to be considered a small town by the criteria I have set for myself on this blog (39,728 in 2019), I want to showcase it as it does still have a small town charm and vibe that attracts so many people to it, myself included. I fully embrace that I have a bias towards Annapolis in that it is one of my favorite places to visit and it will feature prominently on this blog in between posts about other small towns within the state. Not all the time, of course, but enough. I swear I am not on the tourist committee for the town (yet).
Due to the prior COVID-19 restrictions, large scale festivals and celebrations were put on hold in 2020. 2021 marks a return to some semblance of normalcy we saw pre-pandemic, and the Fourth of July holiday weekend was home to more than a few celebrations: live music, dancing in the streets, Tall Ships at the City Docks, tours of some of the historic mansions, the Fourth of July parade in both Annapolis and the bordering neighborhood of Eastport, and of course, the First Sunday Arts Festival.
The First Sunday Arts Festival takes place on the first Sunday of every month from May through November from 11 AM-5 PM. In December, it changes to the Chocolate Binge Festival, and goes from noon-5 PM. The event began in 2001 and has grown to feature over 100 local vendors/artisan stalls on Calvert and West Streets. Walking through the festival area on the sunny 4th of July morning, I was excited to see just how many local artists had their items on display: photographers, painters, bonsai artists, jewelry makers, potters, even a fudge stall. The stalls were flanked by numerous restaurants, offering lots of food to eat, and abundant outdoor tables to eat at. Different musicians had set up in different areas, and so at any given time you might hear some rock music or splashy jazz, or anything in between as you took in the Festival.
My friend and I perused through, stopping at stalls that held our attention, and making mental notes to come back to some specific places. We stopped at a stall run by Randalia Farms, selling farm fresh honey, natural body care products, and some other products made from honey, such as soap and lip balm. My friend bought a large jar of honey, and I bought 3 lip balms (3 for $5): coconut, peppermint and mint julip, before we left the Festival area in search of some lunch.
Because COVID is still very much a thing, and despite being fully vaccinated, I wanted to get food to takeaway and eat in a less crowded area. We walked down to the City Docks, and stopped at Pip’s Dock Street Dogs, close to the Docks, as well as the Naval Academy. This place looks a little like a hole in the wall, but they have incredible food, selling burgers, cheesesteaks, and specialty hot dogs, along with different fries, and they have Jones soda on tap. We took our food down to the City Docks and ate there, enjoying the breeze off of the water. After lunch, we walked over to the edge of the City Docks to look at the boats in the marina and see the Tall Ships, which are replica sailing vessels that would have been seen in the 19th century, one of which is called the Pride of Baltimore II, used to promote historical knowledge of the ships of this era.
Because of the heat, we walked back up the hill to get ice cream from The Red Bean, a specialty ice cream which also offers coffee and tea. I got a waffle cone with vanilla ice cream and Reese’s peanut butter and M&M mix ins, and my friend got an affogato (vanilla ice cream topped with hot espresso in a cup), which we enjoyed on a bench in front of the State House, shaded by old growth trees. Once the treats were done, we walked back to the Festival and stopped by two other stalls we had seen before: I got 3 maps from the stall for Wimsey Cove Maps and Art: a 1560 view of London, a map of the New England states, and a map from at least the 1700’s showing Maryland and Virginia, and my friend got some floursack napkins from a nearby stall for her kitchen. This done, we left the Festival, but there are more than a few places I want to come back and see on another First Sunday weekend.
All in all, Annapolis is a fun place to spend an afternoon or a day, and aside from the places highlighted in this blog post, there are numerous other places I would like to feature on the blog. I think its safe to say that Annapolis will be a recurring place on the blog, in between the posts about other small towns. As always, enjoy the journey!
Pip’s Dock Street Dogs- 118 Dock Street, Annapolis, MD 21401
Hours: Tuesday-Friday: 11 AM-4 PM, Saturday and Sunday: 11 AM-5 PM
Website: http://www.pipsdogs.com
The Red Bean- 220 Main Street, Annapolis, MD 21401
Hours: Tuesday- Saturday: 9 AM-10 PM, Sunday: 9 AM-5 PM
Website: https://www.theredbeanannapolis.com
[1] Leonard M. Adkins, An Explorer’s Guide to Maryland (The Countryman Press: Woodstock, Vermont, 2013), 257.






















