Annapolis Spring Sail Boat Show
April 28th through April 30th; Annapolis City Docks
With a long sailing tradition in Maryland and the Chesapeake Bay, the Annapolis Spring Sailboat Show rings in the new season by bringing together sailing enthusiasts from around the Mid-Atlantic. Every April, guests experience an in-water show boasting the sailing industry’s latest boats, gear, and tech. Comparing side-by-side and talking with industry leaders enables all buyers to have the opportunity to easily and efficiently purchase their next new vessel.
April 28th and 29th; Downtown Easton
Easton will be decked out in flowers, bows, and bouquets for a lovely spring celebration. Merchants will be competing for the "Best Dressed." Come see our winners on Saturday and vote for your favorite, too! One lucky participant will win a Discover Easton prize package.
Land Jam - Presented by the Eastern Shore Land Conservancy
April 29th; Wye Island National Resource Management Area, Queenstown
LandJam is back! Join us on Saturday, April 29, 2023, at the Wye Island National Resource Management Area from 1 to 4 pm to celebrate the land of our beautiful, bountiful Eastern Shore! This family-friendly event will feature live music from Justin Singleton and the Shorebillies, in addition to local food, drink, crafts, and outdoor recreation. To learn more (and reserve your tickets), check out the events page on our website.
Tickle My Money Bone Comedy Event
April 29th, 6:30 p.m.; Virtual Event
Join Crusaders 4 Change for the 3rd Comedy Event virtually! Mix and mingle with Live DJ, comedy hour with professional comedians, and a wrap up party to follow!
April 29th, 7 a.m. to 3 p.m.; Bacon Ridge Natural Area, Crownsville
Join Scenic Rivers Land Trust for our signature community event celebrating the joy of the outdoors and our local, protected woods. Enjoy a day of guided hikes exploring the heart of the permanently conserved Bacon Ridge Natural Area in Crownsville. Experts in wildlife, native plants, birds, and more will be on-site and available to attendees. Plus, self-guided hike options will be offered, complete with trail maps and educational signage posted along the trails, as well as other fun educational activities.
April 29th; The Key School, Annapolis
The Annapolis Book Festival Is Celebrating 20 Years! The Annapolis Book Festival is free to attend and open to all! Every year thousands of people enjoy this community Festival that celebrates the beauty, power, passion, and excitement of the written word. The Festival will celebrate its 20th year in 2023, bringing nationally renowned authors to the community to discuss their books and the craft of writing and featuring a day filled with children's activities, live music, food, and a huge used book sale.
Chesapeake Cycling Club: Tri-County Classic
April 29th; Talbot County Community Center, Easton
Chesapeake Cycling Club's spring cycling event on the Eastern Shore is here! Choose a 100 miles, 65, 36, or 23 mile race which all start and finish at Talbot County Community Center. There will be an ice cream pit stop, food trucks, bands, beer, giveaways and more
April 29th, 10 a.m. to 3 p.m.; Annapolis Town Center
Mangia, come hungry! Enjoy this free, family friendly Italian Festival of Spring with Annapolis Town Center and the Sons and Daughters of Italy Annapolis Lodge. Proceeds from this event will go to support local charitable organizations: The Light House Shelter and Anne Arundel County Food Bank. Homemade Italian Foods and Libations: The lodge bakers will have a variety of Italian cookies, cakes, cannoli and much more for purchase. The lodge chefs will be serving up our Famous Meatball and Italian Sausage subs, and our bartenders will serve Italian specialties for purchase.
Pirate's Parlay of the Chesapeake
April 29th, 12 to 9 p.m.; Anne Arundel County Fairgrounds, Crownsville
Help support the Anne Arundel County SPCA with two days of Pirate Adventure with pirate encampments, live Mermaids, Magic, Music and Mayhem! Beginning with Pirates on Parade at 10 AM Saturday morning as the official start of Maryland’s festival season! Then join us for a great family friendly festival with a large Kids Zone that includes rides, carnival games and a petting zoo and interactive creations with the Chesapeake Children’s Museum. The Pirate stage with Captain Jack and friends. Pig Races and our Dachshund Dashers Hot Dog Races. The older crew can enjoy 40 vendors of food and merch, arts and history displays by local museums, Glass Blowing and Blacksmith demonstrations, Raffles to support the SPCA and more. Strolling artists including jugglers, stilt walkers, magicians and dancers.
April 29th, 8 a.m.; Camden Yards, Baltimore
Join the Erin Levitas Foundation (ELF) on Saturday, April 29, 2023, for the 4th annual Erin Levitas Foundation Stroll & Roll. Friends, families, businesses, and individual supporters will walk, run, dance, stroll or roll to raise awareness about body safety and boundaries to stop sexual harm before it happens. Participants can join in-person in Baltimore or virtually from anywhere around the world.
April 29th, 8:30 a.m.; Terrapin Nature Park, Stevensville
Talisman Therapeutic Riding is hosting their inaugural 5k benefit race! Come get in the spirit for one of Talisman’s signature fundraising events, Derby Day. This will be a fun run that is off road and through the scenic Terrapin Park trail, overseeing the beautiful Chesapeake Bay. Participants are welcome to run or walk! Check in opens at 8:30 am and the official start of the race will be 10 am. Refreshments will be provided for all participants. The event will occur whether rain or shine so be sure to dress accordingly. Come join us for some fun!
April 29th, 10 a.m. to 11 a.m.; Severna Park Community Center
Join Jing Ying Institute as we participate with others around the world to practice tai chi & qigong in friendship & wellness during this annual, international event. There will be demos of Tai Chi & Qigong and mini-workshops. Learn more about better balance, reduced stress, improved joint health, & other benefits. Suitable for all ages and levels of fitness.
7th Annual Lip Sync Battle Fundraiser
April 29th, 7 p.m.; Waterfowl Festival Building, Easton
Talbot Interfaith Shelter's 7th Annual Lip Sync Battle Fundraiser is underway! This year's event will be LIVE at the Waterfowl Building in Easton on Saturday, April 29th, 2023. You can help determine the winners by voting TODAY!
April 30th; Wimsey Cove Framing and Gallery 57 West
Clear out your supplies and give a beginner a head start through the first ArtScrapAnnapolis. The Annapolis Arts Alliance is collecting good quality new / used art supplies to be donated and sold!
Four Rivers Garden Club 78th Annual Flower Mart
April 30th; Maryland Hall, Annapolis
Baskets for May Day, Custom and Ready-Made May Baskets. Pre-order & Day of the Event. Small floral arrangements and posies. Make your own basket- email for information. Perennial Plants from Our Gardens, Native Perennials, Local Garden favorites, Treasures from the Garden Shed & Attic, Containers, baskets, Garden and patio accessories, tools and more. Hand decorated oyster shells and other gifts for Mother’s Day
April 30th through May 1st; The Old Brick Inn, St Michaels
WineFest at St. Michaels and The Old Brick Inn host exclusive wine-tasting weekends featuring small-production wines from popular producers in Europe and the U.S. The tastings focus on wines that are in high demand, but not easily found either online or in area retail stores. The tasting format will be a “wine tour” of some of the very best wine-producing regions of Italy, Bordeaux, Burgundy, Spain, California, Oregon, and South Africa. Come join us for a weekend of tasting fine wines along with learning about specifics of terroir, weather, cultivation techniques and harvest/vinification. We will be featuring some surprise guests to offer their expertise in guiding you through the perspective of how the same grapes can produce such different wines.
April 30th, 9:30 a.m. to 10:30 a.m.; Talisman Therapeutic Riding, Grasonville
Talisman Therapeutic Riding is officially kicking off our wellness program! For the first time ever we will be offering yoga on the farm. Multiple class options will be available this spring! Our first session will be a "Spring tune up, tune in". This 4 week series will take place April 16th, 23rd, 30th, and May 7th. There will be a journal included in this class for meditation and personal use. Classes will be held from 9:30am - 10:30am.
Annapolis ROCKS and Gaithersburg ROCKS
April 30th, 2 p.m.; Maryland Hall, Annapolis
Annapolis and Gaithersburg ROCKS, local rock & roll ensembles with Encore Creativity for Older Adults, will perform a free spring concert alongside a live rock band at Maryland Hall on April 30 at 2 PM. Conductors Jeff Dokken and Ethan Lolley will lead the group through a repertoire of choral arrangements of toe-tapping classics, such as Love Me Tender, Africa, and If I Could Turn Back Time. The concert is the final stop on Encore Creativity's ROCK Tour, which will draw Encore ROCKers from across the region together for large-scale concerts. Tickets are free with a pay-what-you-wish option. For more information and for tickets, go to https://encorecreativity.org or call 301-261-5747.
Sunday Social: Poetry in the Paca Garden
April 30th, 2-4 p.m.; William Paca House and Garden, Annapolis
We’re celebrating National Poetry Month with Maggie Benshaw, Poet Laureate of Annapolis. Join us for an afternoon of poetry in the picturesque Paca Garden. Participants will have the opportunity to compose their own poems in our beautiful garden oasis, and then present their poetry to the audience during our special poetry open mic.
May 1st; Downtown Annapolis
Join in the fun! The Garden Club of Old Annapolis is inviting residents and business owners in the Historic District and parts of Murray Hill to join in the 68th annual May Day celebration by displaying colorful baskets of flowers in front of their houses or business. In addition to baskets, merchants can use containers that are relevant to their business. Baskets need to be displayed by 10:00 AM when members of the Garden Club will begin walking around town to judge the arrangements. Winners (both residential and business) will be awarded blue ribbons and invited to a tea held at local home downtown on May 3rd.
Santa Maria Cup: A Women's Match Racing Regatta
May 1st through May 3rd; Eastport Yacht Club, Annapolis
Eastport Yacht Club will again host the Santa Maria Cup regatta in May 2023. We are proud to resurrect hosting this regatta. The Santa Maria Cup will also be the second stop on the Women’s World Match Racing Tour.
22nd Annual Tee Up For a Child
May 1st; Crofton Country Club
CASA of Anne Arundel County is hosting their 22nd Annual Tee Up for a Child Golf Tournament on May 1st!
