Mother’s Day weekend is around the corner, and there’s no shortage of ways to celebrate, connect, and enjoy the season. From live music and creative workshops to shopping events, outdoor experiences, and meaningful ways to give back, this week’s lineup offers something for every mood and moment. Whether you’re planning a night out, a relaxing day, or time with family, there are plenty of opportunities to make it special. Take a look and start mapping out a week filled with fun, connection, and a little something for everyone.
Colin James, Matt Andersen, & Terra Lightfoot
May 6th; Rams Head on Stage, Annapolis 8:00pm
Enjoy an unforgettable night of powerhouse performances featuring three acclaimed artists at the top of their craft. Blending blues, folk, soul, and rock, the lineup delivers a rich mix of musical styles and standout songwriting. Each artist brings their own unique energy to the stage, creating a dynamic and engaging live experience. It’s a must-see show for music lovers looking for a night of incredible talent and unforgettable sound.
Children's Book Drive
May 6th – 18th; Junior League of Annapolis Office, Annapolis 12:00pm
Help inspire a love of reading by taking part in this community children’s book drive. Donations of new or gently used books will support summer reading and help expand access to books for families in the area. It’s a simple way to make a meaningful impact and encourage literacy in the community. Clear out your shelves and pass along stories to the next generation of readers.
Spring Girls Night Out
May 7th; Homestead Gardens, Davidsonville 5:00pm
Grab your friends and enjoy a lively evening of shopping, sipping, and seasonal inspiration at this annual spring favorite. Guests can browse everything from plants and home décor to unique gifts while sampling local food and drinks and enjoying live music. The festive atmosphere makes it easy to relax, explore, and find something special for the season. It’s the perfect excuse for a fun night out filled with great finds and even better company.
Paca Girlfriends Shopping Night
May 7th; Museum of Historic Annapolis, 4:00pm
Grab your friends and enjoy a fun-filled day of shopping and sipping in downtown Annapolis. Stroll through local boutiques in search of the perfect outfit, unique accessories, and thoughtful gifts for all your upcoming celebrations. Along the way, enjoy festive drinks and a lively atmosphere that makes the experience even more special. It’s a great excuse to explore, treat yourself, and make a day of it with friends.
MANDALA PAINT NIGHT
May 7th; Julep Kitch & Bar, Annapolis 6:30pm
Unwind and tap into your creativity at this relaxing and welcoming evening experience. Designed for all skill levels, guests can enjoy a fun, low-pressure environment that encourages self-expression and connection. Whether you come with friends or on your own, it’s a great opportunity to slow down, try something new, and meet others. Leave feeling refreshed, inspired, and a little more connected.
Mother’s Day Pop Up Tour
May 7th; Annapolis Town Center, Annapolis
Treat yourself (or the moms in your life) to a full day of shopping, sipping, and self-care at this Mother’s Day pop-up experience. Featuring a collection of local favorites, guests can explore beauty services, boutique finds, and relaxing experiences all in one place. The atmosphere is fun, fresh, and perfect for a little spring refresh with friends. It’s an easy, feel-good way to celebrate, unwind, and enjoy a day that’s all about you.
Encore ROCKS Annapolis Concert
May 7th; Mayland Hall, Annapolis 7:00pm
Enjoy a high-energy concert filled with classic hits and feel-good favorites at this lively community performance. Featuring a talented group of singers backed by a live rock band, the show brings together music from across the decades for a fun and nostalgic experience. It’s a celebration of creativity, connection, and the joy of performing at any age. Come out, enjoy the music, and support a program that keeps the arts alive and thriving.
Spring Garden Ramble
May 8th; Historic London Town & Gardens, Edgewater 6:00pm
Take a leisurely stroll through blooming gardens while enjoying an evening filled with live music and relaxed springtime charm. As you wander, you’ll discover musicians tucked throughout the landscape, creating a unique, immersive experience around every corner. With a signature cocktail in hand and beautiful views all around, it’s the perfect setting to slow down and soak in the season. Come for the music, stay for the atmosphere, and enjoy a night that feels both easygoing and unforgettable
Mad Cute Market
May 9th; St. Phillips, Annapolis 11:00am
Step into a fun, fashion-forward market designed for vintage lovers and creative spirits. This vibrant event brings together a curated lineup of woman-owned small businesses offering everything from Y2K and true vintage clothing to handmade goods, jewelry, and art. Guests can enjoy unique experiences, sweet treats, and a lively, social atmosphere while browsing one-of-a-kind finds. It’s the perfect place to dress up, connect with friends, and discover something special you didn’t know you needed.
Talbot County Tour of the Maryland House & Garden Pilgrimage
May 9th; Talbot Historical Society, Easton 10:00am
Step back in time with this special historic tour showcasing some of Talbot County’s most remarkable and rarely accessible properties. Guests can explore stunning waterfront homes, beautifully preserved interiors, and private gardens that offer a glimpse into centuries of history. Along the way, discover significant landmarks and stories from the region’s colonial past through a unique, self-guided experience. It’s a fascinating and immersive outing for history lovers and anyone looking to experience the Eastern Shore in a new way.
AACC Big Band Jazz- Spring 2026 Concert
May 9th; Anne Arundel Community College, Arnold 7:30pm
Enjoy a lively evening of jazz as AACC’s Big Band takes the stage for a night of standout musical performances. Featuring talented musicians and dynamic arrangements, the concert blends classic big band energy with impressive solo moments. The upbeat atmosphere and rich sound make for an engaging experience from start to finish. It’s a perfect outing for music lovers looking to enjoy a night of live entertainment.
Mother's Day Floral Workshop "A Blooming Good Time!"
May 9th; Harvest Thyme Tavern, Davidsonville 1:00pm
Celebrate Mother’s Day weekend with a relaxing and creative floral workshop designed for a fun afternoon out. Guests can enjoy a hands-on experience creating a beautiful arrangement with fresh seasonal blooms, guided step-by-step in a welcoming setting. With a glass of something bubbly and the option to linger over lunch or dinner, it’s an easy way to turn the day into a full outing. Whether you come with friends or treat yourself, it’s a lovely way to unwind and get inspired.
Grand Opening Celebration
May 9th; FS8, Severna Park 11:00am
Celebrate the opening of a new fitness space with a fun and welcoming community event. Guests can stop by to explore the studio, learn about a variety of workout styles that blend strength, flexibility, and movement, and meet the experienced trainers behind it all. With an open house atmosphere and opportunities to see what classes are all about, it’s a great way to discover a new approach to fitness. Whether you’re a regular or just curious, it’s an easy and energizing way to get involved.
Meditation with the Donkey Herd
May 9th; Campbell’s Lane Farm, Easton 9:00am
Slow down and unwind with this peaceful guided meditation experience set in a calm farm environment. Guests can relax into quiet stillness while enjoying gentle guidance and the unique presence of a nearby donkey herd. The tranquil setting creates a soothing space to disconnect from the everyday and reconnect with yourself. It’s a refreshing and memorable way to find calm, clarity, and a deeper sense of relaxation.
Mommy & Me, Bunnies & Tea - Pre-Mother's Day Boutique Farm Event
May 9th; Holiday Memories Farm, West River 3:00pm
Celebrate Mother’s Day with a sweet and memorable farm experience designed just for moms and little ones. Guests can enjoy a relaxed afternoon filled with cuddly bunnies, light bites, and refreshing drinks in a charming picnic-style setting. With time to craft, connect, and soak in the peaceful farm atmosphere, it’s a special way to slow down and enjoy quality time together. A perfect outing for making meaningful memories before the holiday.
Mother's Day at the Farm
May 10th; Honey Harvest Farm, Lothian 11:00am
Celebrate Mother’s Day with a relaxing and joy-filled day on the farm, perfect for the whole family. Guests can enjoy a delicious lunch, fresh baked treats, and scenic picnic views while kids explore, play, and meet friendly farm animals. With live music, local wine, and hands-on experiences like creating your own bouquet at the flower bar, there’s something for everyone to enjoy. It’s a laid-back, feel-good way to spend time together and make lasting memories in a beautiful outdoor setting.
Mother's Day Brunch at Kent Island Resort
May 10th; Kent island Resort, Stevensville 9:00am
Celebrate Mother’s Day with a beautiful brunch experience designed to make her feel truly special. Guests can enjoy a delicious spread of seasonal dishes, sweet treats, and sparkling beverages in a relaxed and elegant setting. It’s the perfect opportunity to slow down, gather with loved ones, and savor quality time together. Thoughtful, welcoming, and full of charm, it’s a lovely way to honor the women who mean the most.
