Summer Fun Guide 

Ideas to fill your summer bucket list 

By Kathy Knotts 

Depending on how you count it, summer is about 100 days, from Memorial Day weekend to Labor Day. It sounds long, but in reality that’s just 15 weekends to squeeze in all there is to do each summer. We’re here to make it a little easier to start filling in your calendar. While this is by no means a comprehensive list of everything happening this summer, it’s your jumping-off point to planning your 100 days of fun in the sun (or indoors in the air-conditioning). 

Time to Come Together 

There are no shortages of festivals, parades, and community gatherings this summer in Bay Country. The unofficial beginning of summer is Memorial Day. This year, gather with friends and family at the Annapolis Memorial Day Parade May 30 at 10am. The parade follows the usual route, from Amos Garrett to City Dock. In Chesapeake Beach, stop by the Veteran’s Park for the annual Stars and Stripes Festival (details in Bay Planner). The Deale Area Historical Society also hosts its Memorial Day Remembrance in honor of generations of local veterans May 30 (10am) at Cedar Grove UMC’s Veterans Memorial. 

June is Pride Month and Annapolis celebrates with a parade and festival (June 4). This year’s theme is Many Faces, One Pride to recognize that the “LGBTQ+ community is comprised of many people, all skin tones, genders, sexualities, religions and abilities,” states Joe Toolan, Annapolis Pride Board chair. The parade steps off at noon on West Street to Amos Garrett Blvd. to Calvert Street and Clay Street. The festival runs till 5pm on West St. between Calvert and Church Circle, the People’s Park and adjacent parking lots. Hear guest speakers, watch dance groups and listen to live music on multiple stages. Graduate Annapolis Hotel hosts a 21+ party with games, DJ, and drag performances. After parties are in the works, too. Details: 

Head to Deale June 4 if you have a hankering for some barbecue. Smokin’ on the Creek returns to Hidden Harbour Marina in Deale with its 4th annual amateur backyard BBQ competition. Live music begins at 11:30am and the Senior Dog Sanctuary will be on site with adorable furry friends looking for a home. Test your skills at the cornhole tournament or play some games. While you can’t sample the contest goods, other food vendors will be selling barbecue. Entry is $15, cash only:

Also June 4, The Friends of St. Clement’s Island & Piney Point Museums present the third annual RetroFest on the Potomac (11am-5pm) at Piney Point Lighthouse Museum & Historic Park. This event is in conjunction with the nearby Southern Maryland Boat Club’s Piney Point Regatta and features classic cars, vintage treasures, live music, food and drink, and free admission to the museum, lighthouse and historic park: Facebook @1836Light

June 11 is time for the 32nd annual Strawberry Festival with the Ann Arrundell County Historical Society. Visit the Benson-Hammond House (10am-3pm) and enjoy all your favorite strawberry treats: wine, jams, shortcake, chocolate-covered and more:  

This year, Chesapeake Country takes Juneteenth to a new level. In Annapolis, there will be a ticketed VIP gala June 17 ($100) and then Saturday a parade and festival beginning at City Dock at noon and ending at the Bates Athletic Complex where you an enjoy live music, entertainment, food, vendors and fireworks. Details:

In Calvert County, the NAACP hosts its annual Juneteenth Celebration June 18 at Jefferson Patterson Park (11am-5pm) which includes a talent contest, food and merchandise vendors and community exhibits:

Bring your appetite to Navy-Marine Corps Stadium Aug. 5 (5-8pm) for the Annapolis Rotary Crab Feast. The 2022 feast will return to its traditional format, so prepare to eat all the crabs you desire in good conscience, knowing that your ticket purchase becomes money for grants made to local charities. Dine on hot steamed seasoned crabs, vegetable crab soup, BBQ, watermelon, corn and cold beverages. Tickets will go fast, $90 w/discounts:

The Maryland Renaissance Festival returns to Crownsville August 27. Take a trip back to Tudor England at this annual royal affair. At opening weekend, kids 15 and under admitted free. Perhaps you’ll meet King Henry VIII and his betrothed Jane Seymour, who will be his third wife—once they execute Anne Boleyn. Tour Revel Grove, eat giant turkey legs, see jousting knights, juggling fools and lovely ladies-in-waiting. It’s even more fun when you come in costume — or rent at the fair. 10am-7pm SaSu, 1821 Crownsville Rd., $21 w/discounts (price increases Sept. 18):  

Watch modern day knights and maidens wield their lances as they gallop down a 160-yard track, spearing three small rings at breakneck speeds. Watch jousters aim for precision victories at the 155th Jousting Tournament at Christ Church in Port Republic. This competition is the oldest and often biggest jousting event in Maryland. The historic event includes a church bazaar, a country supper, music and lots of fun and cheer. The State Sport starts in grand style with knights and ladies parading on their armored steeds onto the field of competition. Colorful cloth seals symbolizing hometowns or family names embellish saddles. Knights are called forth to charge into the games as a trumpet blasts above the fanfare. Knights and ladies compete equally, vying for the title in each of four divisions as they aim for the hanging rings. The winners are crowned at the grand coronation ceremony that ends the day. Aug. 27 at noon, Christ Church, Port Republic: 

Art All Around 

Early June is a busy time on the art scene in Chesapeake Country. June 5 thru 12 is Annapolis Arts Week, an annual celebration that supports the diverse talents of the local arts community with events throughout the region ( Drop in to ArtFarm for workshops for artists of all ages and abilities, including a Slime Workshop and Experimental Painting and Drawing. Other artsy classes and workshops will be held at Maryland Hall and Annapolis area libraries. The week kicks off with a picnic June 4 at MC3’s Park Place lawn (5:30pm). June 5, head to City Dock’s Susan B. Campbell Park to see Dueling Brushes (9am-noon), a quick draw event that gives artists just three hours to create and complete a work. That same day, over on West and Calvert Streets, it’s the First Sunday Arts Festival for even more art on display, special performances and vendors. 

Many Annapolis galleries will have special receptions and events during the week. Stop by Gallery 57 West, home of the Annapolis Arts Alliance to see artists demonstrating jewelry and pottery making June 11 during Dinner Under the Stars (6-9:30pm). 

Scheduled to coincide with Annapolis Arts Week, the Maryland Federation of Arts brings artists to the streets for Paint Annapolis, June 5 through 10. Thirty juried artists from all over the globe come to town to paint in plein air (outdoors). Maryland Avenue will become their outdoor gallery June 9 for Art on the Avenue, which includes live music, food trucks, performances and art demos.  Works will be on display at Circle Gallery and the Pop Up Gallery: 

On June 10, the International Guild of Realism comes to McBride Gallery. You can stop by for a preview of the show featuring 100 pieces by 89 guild members June 10 (6-8pm) or come for the opening reception and awards ceremony June 12 (1-4pm):

McBride Gallery along with The Annapolis Gallery Association also hosts the 32nd annual Annapolis Art Walk August 18. Multiple galleries in Annapolis host live demonstrations by artists, new exhibits and other art-centric events. Stop by the reception for Maria Marino (6-9pm) at McBride Gallery. Details:

Sounds of Summer 

If live music is your jam, then summer is your season to rock out in Chesapeake Country. Beyond all the shows and performances at area restaurants and mid-sized venues like Rams Head on Stage in Annapolis, even area parks get in on the summer music scene. 

In Anne Arundel County, you can catch Guava Jelly playing at Hatton-Regester Green in Severna Park this Sunday (4pm). Beginning June 4, the music moves to Downs Park in Pasadena, through June 26. In July, head to Quiet Waters Park on Saturdays, July 16 through Sept. 3, for the rest of the summer series. These shows are all free, so bring your family and friends, lawn chairs, a picnic dinner and enjoy. Find the full schedule: 

Spend Fridays with the Captain. Captain Avery Museum in Shady Side that is. Each Friday 7-9 pm in June, July, and August watch a different presenter each week. Guests will play music, make art and talk about local history. Refreshments will be available. Details:

Sundays this summer you will find music, tango and salsa dancing at Susan Campbell Park at City Dock in Annapolis, hosted by the Art in Public Places Commission. Details haven’t been posted as of press time, so keep an eye on their social media sites. 

Annapolis Maritime Museum’s popular concert series Tides and Tunes returns this year. Ten weeks of concerts on the water begin June 16. The shows are technically free, but donations are encouraged. 

Now let’s talk big name performers and festivals—a summer staple. 

The Let’s Go! Music Festival hits the AA County Fairgrounds in Crownsville June 3 thru 5. See top acts such as Lynyrd Skynyrd, Jimmie’s Chicken Shack, Billy Currington, Jimmie Allen, the Goo Goo Dolls, Better Than Ezra, and many more at this outdoor music festival. You can purchase day tickets or three-day passes. Gates open at 5:30pm Friday, noon Saturday, 12:30pm Sunday and close at 11pm each night (10pm Sunday). Tickets and more: 

Want to do good while enjoying live music and libations? Head to Bands in the Sand which benefits the Chesapeake Bay Foundation. This year’s headliner is G. Love & The Juice, with local acts Misspent Youth and Swamp Donkey. Show begins at 5:30pm, June 11—carpool or ride shares encouraged as parking is tight at the CBF headquarters (6 Herndon Ave., Annapolis). While the ticket price may seem a bit steep (starting at $200) it is all-inclusive—food and drinks are included! Details: 

See Derek Warfield and the Young Wolfe Tones in concert at Killarney House Irish Pub in Davidsonville June 21 & 22 (7:30pm). Featuring traditional ballads and original songs, these native Irish musicians are sure to bring banjo, bodhrán, guitars and high energy for an experience rich in the history and tradition of Ireland.  Limited seating, so get your tickets now ($25) at 

Celebrate local, original music at Eastport a Rockin’, a homegrown music festival featuring over 30 bands and nonstop tunes. This Chesapeake favorite returns June 25 (11am-8pm) on Back Creek at the end of Second Street in Eastport. Food and drink vendors on site; proceeds benefit local nonprofits. Tickets on sale now: 

Calvert County gets in on the summer vibes when Calvert Marine Museum opens its PNC Waterside Music Series in Solomons. CBM Bay Weekly is a sponsor of this popular series, which brings big names in music to Southern Maryland. June 10 see Old Dominion, July 16 Deale natives The Brothers Osborne, and August 20 it’s The Beach Boys with The Temptations. Follow us on social media for the chance to win tickets to all of these concerts! Tickets: 

For something a little different, return to the museum’s waterfront stage to hear the Baltimore Symphony Orchestra July 30. The BSO is on its Music for Maryland tour and will perform a variety of crowd favorites as they wander from the mountains to the sea this summer. Tickets are pay-what-you-wish: 

Head over to St. Mary’s College of Maryland for the River Concert Series presented by the school and the Chesapeake Orchestra. A Southern Maryland tradition now in its 24th season, this family-friendly music festival, and winner of two Governor’s Awards for Arts, Tourism, and Community Economic Development will be held on the St. Mary’s College Townhouse Green. Main stage programs are Fridays at 7 p.m. starting on June 24, and continuing on July 1, 8, 15, and 22. Regretfully, this year they are not able to offer fireworks. The concerts and parking are free and open to the public. Details: 

The Potomac Jazz & Seafood Festival comes to St. Mary’s County, July 8-10. This award winning three day weekend event featuring a variety of national and regional jazz acts takes place along the Potomac River at St. Clement’s Island Museum and across venues at businesses in historic Leonardtown. Lots of seafood, parties, receptions and other jazz fun happen during the festival weekend. Jazz cruises around St. Clement’s Island State Park, Maryland’s first colonial landing in 1634, are offered as an optional experience. Proceeds benefit St. Mary’s County museum education programs, preservation projects, exhibits, matching grants and more. Details:  

The Great Outdoors 

During the summer months, the great outdoors beckons. In Chesapeake Country, we are blessed with great state and local parks, many of which host events all summer long. 

Get a jumpstart on celebrating Great Outdoors Month by joining a ranger to celebrate National Trails Day June 3 at Sandy Point State Park. Listen to the songs of frogs as you learn backpacking basics and the many ways you can minimize your impact on the great outdoors (7pm, $5+ day use fee, RSVP: 410-974-2149).  

If you prefer a stroll through a garden, mark your calendar for June 4 and 5 when the Secret Garden Tour invites you into private spaces in Spa View Heights. Hosted by The Hammond-Harwood House in Annapolis, the tour will highlight gardens in the area between Murray Hill and Spa Creek. The gardens featured reflect the goals of the home gardeners: to have a beautiful space filled with flowers, trees, shrubs, grasses, and other garden elements, a space that is a pleasure to live in and an inspiration to work in. Each day noon-5pm, proceeds benefit the house museum ($35 w/discounts, RSVP: 

Enjoy the grounds of Annmarie Garden in Solomons during their Enchanted Summer in the Garden. Find a variety of low-touch fun along the trails and paths of the sculpture garden, search for fairy houses, play in the Fairy Lolly nature playspace, search for gems and fossils, find hidden objects and create your own works of art in the artLAB. Annmarie hosts the popular kids event Insectival July 23 (9am-1pm, $8 w/discounts) where guests learn about bugs and insects, both tame and creepy. Details: 

The 35th annual Children’s Day on the Farm is June 5 at Jefferson Patterson Park in St. Leonard (11am-5pm). Celebrate southern Maryland’s rich agricultural heritage with live performances, crafts, games, vendors, petting zoo, demos and exhibits about rural life. Details: 

Catch a Wave 

There may be no better place to be during summer than on the Bay itself. This is the season to pull out your kayak, canoe, stand-up paddleboard or head to one of the many businesses that can get you on the water. 

Sailboat racing is to Chesapeake Country what hockey is to Canada or bullfighting to Spain, except our arena is the Bay. Finding a place to watch (often a waterside bar) is part of the fun. The best parts of the race for land-based spectators are the start and the finish. 

Amateurs race for fun and bragging rights most Wednesday nights all along the water. In Annapolis, over 120 vessels race in the Annapolis Yacht Club’s Wednesday Night Series ( The finish line stretches from the Annapolis Yacht Club over Spa Creek to Eastport. Be at the Spa Creek Bridge around 7pm when 10- and 12-gauge cannons salute the winners of each class.  

In Galesville on the West River, members of the Pirates Cove Race Club ( vie for series trophies in weekly races starting at 6pm. Watch from Pirates Cove, where races begin and end. In Herring Bay, members of the Herrington Harbour Sailing Association ( race starting around 6:30pm. At best, you’ll get a distant view of boats with their colorful spinnakers sailing into the sunset. In Solomons, Southern Maryland Sailing Association ( members race up the Patuxent River starting at 6:30pm.  

If you’d like to paddle rather than sail, head over to Jug Bay Wetlands Sanctuary in Lothian June 4 for their Paddle-A-Thon. From 6am to 6pm, you can put your skills to the test by paddling the Patuxent River, Maryland’s longest river. Choose from a 4.2-mile or 11-mile paddle. Bring your own gear or rent a kayak or paddleboard. Prices vary on length and rentals. After party at Emory Waters Nature Preserve. Details: 

Jug Bay also hosts other paddling events, showcasing the archaeology of the Patuxent, plus wildlife and plant exploration floats, and special canoe excursions for Father’s Day. 

Prefer to have someone else do the driving? Annapolis Maritime Museum, Calvert Marine Museum, Schooner Woodwind, and Watermark all host boat tours and cruises during the summer. We highly recommend everyone take a tour of the Thomas Point Lighthouse at least once. 

Of course, we tend to think summer is about a cold orange or grapefruit crush and dining on crabs on the waterfront. It’s no secret that we are partial to Big Mary’s at Pirates Cove in Galesville. This waterfront dock bar has served South County and the Chesapeake boating community for almost four decades. They’ve been working on some new cocktails for you this summer, including the Hopetown Lime Paloma and Jameson Irish Crush. Pirates Cove is accessible by land or water on the West River in Galesville, a small, walkable village that’s home to a handful of shops featuring antiques and local art. For overnight docking, call Pirates Cove Marina 410-867-3600. For music and special events: 


Wherever you head over the next 100 days, we hope you stop to take in a sunset, sip an ice-cold glass of goodness and savor every memory of summer in Chesapeake Country.