Rainbow Ride
Ride into Pride at Tribe Cycle to kick off LGBTQ Pride Month. All skill levels, ages, and pride attire are encouraged for the indoor ride followed by a champagne toast (for those 21 and older). 5:30 p.m. May 31. 890 C Bestgate Road, Annapolis. Required pre-registration is $28 at tribecycle.zingfit.com. 443-808-1234.
Tom Caraker Memorial Ride
Celebrate the life and service of the late “Mayor of the B&A Trail,” Tom Caraker, and National Trails Day with an easy-paced bike ride. Meet up at 7:45 a.m. June 1 on the trail behind PedalPushers, 546 Baltimore Annapolis Blvd., Severna Park, and start riding at 8 a.m. The group will ride a slow two miles to the ranger station for a short ceremony then gather at the Big Bean. Wear a yellow vest and Lifeline100 shirt if you have one. A tax-deductible donation is encouraged to support a new gathering area in Tom’s name behind Big Bean. Free. Register at evite.me/e2cS8d9N6G.
Get Crooked Fest
Jimmie’s Chicken Shack headlines the show with support from Stolen Rhodes, Yellow Dubmarine, Joey Harkum, and more. There will be food trucks, Great Frogs wine and plenty of craft beer from Crooked Crab Brewing Company, Jailbreak, Hysteria, RAR and Monument City for $5 a pour. 2 p.m.-9 p.m. June 1. Anne Arundel County Fair Grounds, 1450 Generals Highway, Crownsville. The event is 21+ and rain or shine. Tickets are $25 at getcrookedfest.com and $35 at the gate.
Secret Garden Tour
See the private gardens of the Historic District. Find architectural gems from Annapolis’ earliest days, Victorian-era and 20th-century homes with gardens of all shapes and sizes from City Dock to Spa Creek. Noon-5 p.m. June 1 and 2. Hammond-Harwood House, 19 Maryland Ave., Annapolis. Tickets are $30 in advance and $35 the day of the tour. Hammondharwoodhouse.org. 410-263-4683.
‘Love Letters’
Compass Rose Theater presents A.R. Gurney’s “Love Letters,” a two-character play chronicling the tumultuous lifelong friendship of a couple who never marry. The play stars Janet Luby and Rick Wade, a restaurant critic for The Capital. 2 p.m. June 2. Hotel Annapolis, 126 West St., Annapolis. Tickets are $50 per person through the box office at 410-980-6662 or at compassrosetheater.org, or at the door for $55.
Green Drinks at the Garden Theatre
Annapolis Summer Garden Theatre is celebrating its efforts to go green. 5:30 p.m.-7:30 p.m. June 4. 143 Compromise St., Annapolis. Complimentary appetizers and a cash bar will be available. Admission is free, but a donation of $10 is requested. Annapolisgreen.com. 410-703-2697.
Run Your Towne 24 Hour Challenge
Celebrate National Running Day for 24 hours by running or walking the Annapolis Towne Centre for the whole day, just an hour, or anything in between to raise money for Danny’s Fund, part of the Community Foundation of Anne Arundel County with a goal of directing contributions toward changing the course of addiction in the county. 6 p.m. June 5 to 6 p.m. June 6. Registration is $24 at charmcityrun.com.
Rock the Dock
Join the Annapolis Rotaract Club for a summer night of live music, food, drinks and fun overlooking the Chesapeake Bay. 6 p.m.-10 p.m. June 6. Each $70 ticket includes bottomless beer, wine, orange crushes, all-you-can-eat local BBQ, appetizers, and oysters. There will be games, raffles, and a silent auction. Proceeds will support Live Water by Capital SUP Annapolis, advocating for water sports to better the well-being of our communities. Annapolis Maritime Museum & Park, 723 2nd St., Annapolis. Annapolisrotaract.org. 410-295-0104.
