Pleasant weather means the pace of life in Annapolis shifts outdoors, and one of the most pleasant things about the season may be the opportunity to enjoy theater under the stars.

Annapolis Summer Garden Theatre, one of the city’s oldest acting troupes, debuts its 58th season with a production of “The Prom.” The story of four fading Broadway stars who head to a small-town Indiana to save the prom and their careers, the stage musical was made into a 2020 movie that quickly sank from memory, despite starring Meryl Streep and Nicole Kidman.

Annapolis Summer Garden Theatre starts its 2024 season with "The Prom."
Annapolis Summer Garden Theatre starts its 2024 season with "The Prom."

Enough time has passed from that bomb to make a local production from a company well-known for quality productions and a unique setting — the theater sits next to City Dock — worth putting on your calendar. The show runs through June 15. Tickets are $30 plus fees, with group discounts.

Annapolis Summer Garden Theatre produces three shows each season. “Jimmy Buffett’s Escape to Margaritaville” opens June 27 and “Big Fish” on Aug. 8. Shows tend to sell out early.

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If you’re looking for a more casual outdoor setting, Classic Theatre of Maryland will stage its Beer Garden series at Reynold’s Tavern, performing the classic farce “The Miser” from June 18 through Aug. 29. Tickets to the weekly performance are $55-$74.

Classic Theatre won’t be performing its big summer production outdoors this year, instead moving “A Midsummer’s Night Dream” into its West Street theater.

One thing to remember about theater outside is that it rains outside, just as it did back in Shakespeare’s day. Usually, you’ll get a rain check rather than a refund, but it pays to know the policy in case the skies open up on your opening night.

Here are six more things to do in the next seven days.

West Street table

6-10 p.m. Saturday

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Dinner Under the Stars, a popular outdoor dining event that takes place Wednesdays and Saturdays on the first block of West Street, is open for the season.

Seven restaurants serve at tables and chairs set up in the street under twinkling lights. Live music, art exhibits and special promotions from businesses on the street flesh out the event. On Wednesday nights, pickleball courts are marked off in the street.

Dinner Under the Stars continues through Sept. 28. Admission is free.

Drink local wine


I recently wrote that all holidays are made up. Here’s an example: Saturday is National Wine Day.

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OK, if you need an excuse to seek out local wine. Fine. Saturday is as good as any other.

There is only one winery in Annapolis, Great Frogs on Spa Road. It has regular entertainment at its small tasting room on Fridays, Saturdays and Sundays with picnic tables set up next to its vineyard. Madison Bailey, a well-known singer at area venues, will perform from 1 to 4 p.m. Saturday

A little further south, The Vineyards at Dodon in Davidsonville offers guided tastings by appointment, but this season it has added self-guided flights of wine in the picnic area or tasting room on Fridays, Saturdays and Sundays.

Thanksgiving Farm Vineyards and Winery in Harwood opens its sales room from noon to 5 p.m. on Saturdays and Sundays.

If you’re interested in going a little farther from Annapolis, check out Wine Enthusiast’s May review of wineries to visit across Maryland.

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Get in the river

7:30 a.m. Sunday

Open-water swimming becomes more popular as the Chesapeake Bay and its tributaries warm up. Right now, the water temperature is about 64 degrees.

That’s warm enough for the Bridge2Bridge swim in the South River, the season’s first event by Crossing Currents Aquatics. It’s a 3-mile swim between the Route 2 and Riva Road bridges south of Annapolis, with each pod of swimmers accompanied by a dedicated paddler.

A pod is group of two to four swimmers escorted by paddleboarder or kayaker. Swimmers in each group take turns paddling, or can opt for a dedicated support paddler for an additional fee.

Registration is available for pods or individuals, who will be matched with swimmers of similar speed. Base price is $105 per swimmer, with a variety of discounts available.

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Memorial Day

10 a.m. Monday

Annapolis will mark Memorial Day, set aside to remember those who died in uniform during a U.S. armed conflict, with its annual Memorial Day parade.

The parade starts at 10 a.m. at Amos Garrett Boulevard and West Street, then makes its way around Church Circle to City Dock. The Fleet Reserve Club on City Dock will host a Memorial Day ceremony at 11:30 a.m.

Other Annapolis-area Memorial Day observances include 11 a.m. ceremonies at the Maryland World War II Memorial across the Severn River from Annapolis and the Crownsville Veterans Cemetery, 1122 Sunrise Beach Road in Crownsville.

Taste of Pride

4-7 p.m. Tuesday

Forward Brewing owners Cam and Claire Bowdren work with local nonprofits to produce small batches of special beers used for fundraisers, and one of the longest-running series is the annual Pride Beer ahead of the Annapolis Pride Parade on June 1.

This year’s beer is a sour IPA with hints of mango called “It’s Giving Mango.” Admission is free, with beers priced individually.

Day at the races

6:30 p.m. Wednesday

The Blue Angels and the Preakness are gone for another year after this week, but there’s a more sedate example of elegance and power to be found in the Annapolis Yacht Club’s Wednesday Night Races.

The races continue all summer long, with boats starting the course at 6:30 a.m. and finishing in the Annapolis Harbor ... well, when they finish. You can find a spot at City Dock or walk up the Spa Creek Bridge to watch the finish for free.

Or, you could board the Annapolis Maritime Museum skipjack Wilma Lee to watch the boats as they jibe for position around the course. Tickets are $75. Schooner Woodwind I and II take part in the races and offer their own close-up views of the competition. Tickets are $75.25.