I’m writing this fresh off my annual free Rita’s on the first day of spring, which can only mean one thing: summer in Annapolis is right around the corner. And truly, there’s nothing like it. Bay breezes, crab feasts, notorious ice cream flavors, and golden-hour sails. It’s the kind of place people vacation to, but we get to call home. So, I’m rounding up my Annapolis Summer 2026 bucket list — part “how have I never done this?” and part “I will never stop doing this.”
Annapolis Blues Double Header
Shockingly, this falls into my “never done” category. Now that my kids are older and sportier, I can’t wait to catch a Blues game or two this season.
Like our old friend Ted Lasso, the men return for Season 4 in Summer 2026, while the women kick off their second season after an unforgettable debut. I can’t wait for both squads to take the pitch at Navy-Marine Corps Memorial Stadium and be a part of an electric (can you say shellout?) hometown crowd. Grab tickets.
Doubleheaders (men and women playing on the same night) are scheduled for:
May 30 (home opener)
June 21
June 27
Courtesy of Annapolis Blues
Set Sail
We can’t talk about “America’s Sailing Capital” without getting on the water.
Schooner Woodwind: I’ve had many nautical moments, but sailing isn’t one of them. Time to change that. Schooner Woodwind offers public or private cruises.
Watermark’s Harbor Queen: This was such a big hit among all ages at my family reunion. We did the 40-minute narrated cruise past the U.S. Naval Academy, but there are many cruises to choose from.
Pirate cruise adventure: A popular field trip option for a reason — kids (and adults) love this iconic pirate cruise that includes searching for sunken treasure, and firing water cannons at invading pirates.
Watch the Wednesday Night Races (WNR)
If you can’t climb aboard, at least pop a squat on the Eastport Bridge to watch someone else cruise down the Annapolis Harbor. Pro tip: If you’re watching from land, the finish is the best sight to see. Races start around 6 PM and finish in front of the Annapolis Yacht Club.
WNR happens just about every Wednesday night through the end of August.
Photo by Mike Iserman Photography
Act like a tourist downtown
Keep it simple with this recipe for fun: Annapolis Ice Cream + shopping. Just finish your ice cream before going inside. Don’t ask me how I know.
Try Naptown Scoop Dinner Club
Not gonna lie, this is a little out of my comfort zone. You don’t know where you’re eating until the morning of Dinner Club. You don’t know who you’re eating with until you arrive. But over 100 people attended the first one and over 100 are already signed up for the second.
Dinner (and Pickleball) Under the Stars
“Dancing in the Street” is just one of the joyful activities taking place Wednesdays and several Saturday nights on the first block of West Street from May to September. Grab your paddle for a game of pickleball, then a bite, all while enjoying live music and twinkle lights. Don’t forget to make your reservation at the participating restaurants. Tip: Dine on the later side. Take my word for it: it’ll be much cooler once the sun goes down.
Host a raft-up concert
Ryan got invited to one with Pressing Strings a few years ago and I’m still jealous. This is the summer I host my own. Step 1: Buy a boat (or more likely, ask a friend).
First Sunday Arts Festival
Speaking of West Street, the First Sunday Arts Festival is the perfect opportunity to shop local from 100+ vendors. The gorgeous art, plus café dining and live entertainment remind me of a European street market.
Rotary Crab Feast
Of course Annapolis hosts “the world’s largest crab feast.” Last year’s 80th annual feast served 1,100 attendees gathered for an evening of crabs, barbecue, corn-on-the-cob, and plenty of beverages. Out-of-towners say “fest” instead of “feast” because it really is a party. If you need another reason to attend, proceeds go to local charities. Keep an eye on the Rotary’s website for tickets.
Courtesy of Visit Annapolis
Or, if you can’t make it August 7, crack ‘em anytime at Cantlers, Mike’s, or The Point.
Sip the state drink
As of last summer, the orange crush is the official state drink of Maryland. You don’t have to drive all the way to Ocean City to get a good one — we recommend The Choptank, Dock Street Bar & Grill, and Boatyard Bar & Grill.
Attend an outdoor concert
PSA: Don’t forget to BYO chair or blanket! (or even a paddleboard)
Courtesy of Chronic Sailing
Tunesday: Floating concert series on Back Creek? Yes, please! Music plays for 90 minutes and ends around sunset. Shows officially start May 5 (that’s this week!) and run through September 1. See the lineup.
Tides & Tunes: Runs June 11-August 13 at the Annapolis Maritime Museum. Concerts are free; donations are gratefully accepted. Expect food trucks and spirits for sale. Bring or buy a cup — it’s a zero waste event.
Annapolis Town Center’s Thursday Night LIVE!: Everyone can find a night of music to love once this concert series begins June 4. It runs through August from 6:30 to 8:30 PM each night. Enjoy patio dining or grab something from the food or drink tents.
Annapolis Summer Garden Theatre (ASGT)
Every time I pass by, I have the urge to climb the fence and peek in. This summer, I’m hoping to finally bite the bullet and grab tickets. I have an eye on “Mel Brooks’ Young Frankenstein” because the original film always cracks me up.
Courtesy of ASGT, photo by Lauren Winther Hansen
Another outdoor theater option
Compass Rose Theater’s student production of A Midsummer Night’s Dream runs July 31-August 9 at Historic London Town & Gardens. Classic Theatre of Maryland often does weeknight performances in the outdoor courtyard at Reynolds Tavern but details for this year are TBA.
Hot tip (literally): Our in-house theater expert Dylan Roche says Colonial Players’ one-act festival is a great option for those who prefer air-conditioned shows in the heart of downtown.
Fireworks on the water
This might be the worst kept secret in Annapolis but the Sherwood Forest Fourth of the July fireworks are the best in town. And they’re actually on July 3rd. Just one problem.
You have to live in Sherwood or know someone who does to watch from the neighborhood.
Which is why hundreds of boats anchor in the Severn to watch. It’s the best.
Photo: Naptown Scoop
