The last weekend of May is packed with things to do around Coastal Delaware, from beach yoga and live music to local markets, family-friendly fundraisers, food festivals, theatre, brunch, and outdoor adventures. 

Whether you want something relaxed, something lively, or a little bit of both, there are plenty of ways to get out and enjoy the beach towns this weekend.

Delmarva Board Sport Adventures’ Guided Kayak Excursion

Delmarva Board Sport Adventures’ Guided Kayak Excursion is a beginner-friendly way to get out on Rehoboth Bay with help from an ACA Certified Kayak Instructor. 

The guided paddle covers the basics of kayaking before heading through the shallow waterways, where you may spot Osprey, Great Blue Heron, Green Heron, Bald Eagles, and the protected area around Thompson Island. 

People can choose a single or tandem kayak when available, and the excursion is designed for people who want an easy, scenic, and relaxed way to enjoy the bay, sunshine, and coastal breeze.

• Dates: May 29th-31st
• Hours: Various 
• Address: 135 Dagsworthy Street, Dewey Beach

Mary Poppins at Possum Point Players

Possum Point Players is bringing Mary Poppins to the stage with all the magic, music, and heart people love from the classic story. 

Set in London in 1910, the musical follows Jane and Michael Banks after they have sent one nanny after another packing until Mary Poppins arrives and helps the whole family learn how to value each other again. 

With Bert guiding the story and songs like “A Spoonful of Sugar,” “Let’s Go Fly a Kite,” and “Chim Chim Cher-ee,” this is a fun pick for families, theatre fans, and anyone who could use a little reminder that anything can happen if you let it.

• Dates: May 29th-31st 
• Hours: 7:30pm & 2pm
• Address: 441 Old Laurel Road, Georgetown

Rehoboth Beach Sports Card & TCG Show at the Convention Center

The Rehoboth Beach Sports Card & TCG Show at the Convention Center is a free event for collectors, investors, players, and families who want to browse sports cards, trading card games, rare finds, vintage classics, modern collectibles, and memorabilia from vendors across the East Coast. 

The show is being billed as Rehoboth Beach’s first sports card and TCG show, bringing the hobby right into town just a short walk from the shoreline. 

A special highlight is an appearance by Nick Minicucci, hometown hero and starting quarterback for the University of Delaware, with guests able to bring their own items for signatures or photos.

• Dates: May 29th-31st 
• Hours: Schedule varies each day
• Address: 229 Rehoboth Avenue, Rehoboth Beach

Daily Dewey Beach Yoga

Daily Dewey Beach Yoga is back on the sand at Dickinson Avenue Beach, giving people a relaxed way to start the day by the ocean. 

The class keeps things simple: bring a beach towel to use as your mat, settle in on the sand, and enjoy a beach yoga session from a group that has been offering yoga in Dewey Beach since 2017. 

With daily classes running through Labor Day, it is an easy option for anyone looking for a little movement, fresh air, and calm by the water.

• Dates: May 29th-31st
• Hours: 8am to 9am 
• Address: Dickinson Avenue Beach, Dewey Beach

Image: Developing Artist Collaboration

West Side Creative Market

West Side Creative Market is a laid-back open-air market in Rehoboth Beach with more than 20 local artists and makers, rotating food trucks, live music, drinks, and a strong community feel. 

This market is a great stop if you want to shop handmade goods, grab food from Brandylynns or Shore Island, listen to music by Devin Canfield, and support local creatives in a casual outdoor setting. 

It is also family-friendly, dog-friendly, free to attend, and easy to enjoy whether you are going for the shopping, the food, the music, or just the neighborhood vibe.

• Date: Friday, May 29th
• Hours: 5pm to 9pm
• Address: 19826 Central Street, Rehoboth Beach

Fenwick Island Farmers’ Market at The Station 

Fenwick Island Farmers’ Market at The Station is a great Friday stop for fresh, local, and seasonal finds near Fenwick Island, Bethany Beach, and Ocean City. 

This verified producer-only market means vendors are selling only what they grow, bake, or make, so shoppers can browse local produce, flowers, baked goods, and more while supporting area farmers and makers. 

Since the market is set up at The Station parking lot, it is also easy to grab breakfast, coffee, or lunch after shopping.

• Date: Friday, May 29th
• Hours: 8am to 12pm 
• Address: 1406 Ocean Highway, Fenwick Island

Full Moon Party x Decade 80 at Big Chill Beach Club

This party is bringing together live music, dancing, and full moon energy for a fun night by the beach. 

Decade 80 Band will take over the Sunset Lounge with all the big 80s hits, so expect plenty of nostalgia, singing along, and music made for dancing. 

At the same time, the Silent Disco will be happening in the sand pit, where guests can grab free headphones, choose between two curated channels, and dance under the stars with the full moon lighting up the night.

• Date: Friday, May 29th
• Hours: 6pm to 9pm
• Address: 27099 Coastal Highway, Bethany Beach

Say My Name 5k & 1m Walk in Lewes

The Say My Name 5k & 1m Walk in Lewes is a heartfelt event honoring children who have faced cancer while raising awareness and support for pediatric patient rights, care, and research. 

Participants can run, walk, join the Kiddie K, or take part virtually, with dedicated signs along the Cape Henlopen State Park Trail honoring young loved ones and encouraging everyone to say each child’s name as they pass. 

After the race, the event continues at the American Legion pavilion with live music from Catch The Drift, light food, drinks, a silent auction, awards, and a strong community message that no child or family should have to walk alone.

• Date: Saturday, May 30th
• Hours: opens at 7am, starts at 8am
• Address: American Legion Post #17, Lewes

Corinne M. Litzenberg Book Signing at Browseabout Books

Corinne M. Litzenberg will be at Browseabout Books signing Ben and the Brass Check: A Lewes Life-Saving Station Story, a children’s book inspired by local history and the brave surfmen of the Lewes Life-Saving Station. 

The story follows Ben after he finds a brass patrol check on Lewes Beach and meets Levi Lynch, a surfman connected to the dramatic rescues during the Great Blizzard of 1888. 

With archival images, coastal history, and themes of courage, teamwork, and service, this is a sweet stop for families, young readers, and anyone who loves stories tied to Lewes and Cape Henlopen history.

• Date: Saturday, May 30th
• Hours: 11am to 1pm
• Address: 133 Rehoboth Avenue, Rehoboth Beach

Image: Visit Delaware

Southern Delaware Wine, Food, & Music Festival at The Cambria Hotel

The SoDel Fest is bringing delicious food, drinks, music, and community spirit to The Cambria Hotel. 

Guests can sample small plates from area restaurants, enjoy more than 100 tastes including wines, cocktails, mocktails, and craft beers, listen to live music, and check out the festival’s signature Chef Throwdown Competition with mystery basket ingredients and celebrity judges. 

There will also be a silent auction and wine wall, with proceeds helping support local nonprofits, so it is a fun way to sip, snack, and give back in one place.

• Date: Saturday, May 30th
• Hours: 12pm to 4pm
• Address: 17222 Hood Road, Rehoboth Beach

Rally For Our First Responders at Hudson Fields

Rally For Our First Responders at Hudson Fields is all about giving back to the local emergency responders who show up for the community every day. 

The event brings people together for a family-friendly afternoon of fundraising, education, and support, with ways to help throughout the day, including greeting guests at the front gate, assisting in the children’s zone, helping vendors, and lending a hand at the silent auction tent. 

It is the fifth year for the rally, and the mission is simple: honor Delaware’s first responders and help support the people who help keep local communities safe.

• Date: Saturday, May 30th 
• Hours: 12pm to 5pm
• Address: 29763 Eagle Crest Road, Milton

Milton Arts Guild’s New Music & Wind Festival 

The New Music & Wind Festival is bringing free concerts, local art, and a big celebration of jazz composer and saxophonist Julius Arthur Hemphill to Milton. 

The festival features music from Bob Boilen, The Hemphill Stringtet, Janel Leppin’s Ensemble Volcanic Ash, Marty Ehrlich & Guests, and the J.A.H. Jam, along with new works and performances inspired by Hemphill’s legacy. 

Milton Arts Guild artists will also be there exhibiting their work, so visitors can enjoy live music, local creativity, and the energy around MAG’s new education and event venue, MAG ArtSpace.

• Date: Saturday, May 30th
• Hours: 2pm to 8:30pm
• Address: 612 Federal Street, Milton

Beach Driving Clinic at Indian River Life Saving Station

The Beach Driving Clinic at Indian River Life Saving Station is a helpful hands-on program for anyone who wants to feel more confident driving on the sand. 

Park staff will go over beach driving rules, licensing requirements, required equipment, and safety tips before leading participants out to the beach to practice in real conditions. 

It is a practical way to learn what you need before heading onto the sand, especially for newer surf tag holders or anyone who wants a refresher before beach driving season gets busy.

• Date: Saturday, May 30th
• Hours: starts at 9am
• Address: 25039 Coastal Highway, Rehoboth Beach

Live Music at Paradise Grill

Live Music at Paradise Grill is a beachy, tropical way to spend time on the Indian River Bay with food, drinks, and entertainment in a relaxed Long Neck setting. 

Paradise Grill is known for its island-inspired atmosphere, palm trees, salt air, family-friendly energy, and a full lineup of live music and events. 

This weekend’s Beach Stage lineup includes Matty Q, DJ Gregg, and The Saints, giving guests a full afternoon and evening of music to enjoy with friends, kids, cold drinks, and that classic waterfront feel.

• Date: Saturday, May 30th
• Hours: starts at 3pm
• Address: 27344 Bay Road, Millsboro

Image: Nalu Surf Bar & Grill

Summer Shows at Nalu Surf Bar & Grill Dewey

Summer Shows at Nalu bring live music to an open-air spot known for its Pacific island fusion menu and fun beach-town atmosphere. 

This weekend’s lineup includes Decade80, a high-energy band that fully leans into its “we own the 80s” vibe, along with Matty Q, a singer and songwriter who started out fronting the Philly party band SPEED before going solo and later releasing his debut album, Another Key West Night. 

This is an easy pick for anyone looking to pair dinner, drinks, and live music in Dewey Beach.

• Dates: May 30th & 31st 
• Hours: 9pm to 12am & 6pm to 10pm
• Address: 1308 Coastal Highway, Dewey Beach

Piano Show & Sing-Along in The Treehouse Lounge at The Pines

The Piano Show & Sing-Along in The Treehouse Lounge at The Pines brings a lively, interactive night to one of downtown Rehoboth Beach’s cozy upstairs spots. 

The Treehouse Lounge comes alive with strong vocals, sing-along favorites, crowd requests, cocktails, bites, and the kind of upbeat atmosphere that makes it easy to settle in and stay awhile. 

That’s a great choice for anyone who wants music, drinks, and a little audience participation without needing a big concert setting.

• Date: May 30th & 31st
• Hours: 6pm to 8pm & 6pm to 9pm
• Address: 56 Baltimore Avenue, Rehoboth Beach

Full Moon Beach Yoga & Bonfire in Dewey Beach 

Full Moon Beach Yoga & Bonfire in Dewey Beach is a peaceful way to unwind by the ocean with an all-levels yoga session under the full moon. 

The evening starts with a calming flow as the sun sets and the moon rises, with ocean breezes, sand under your feet, and gentle drumming in the background. 

After yoga, the experience continues with a guided crystal meditation, a letting go release around the bonfire, and time to sit and drum with David. 

Bring a beach towel or yoga mat, come solo or with a friend, and settle in for an evening meant to help you reset, relax, and reconnect.

• Date: Sunday, May 31st 
• Hours: starts at 7pm
• Address: Dickinson Avenue Beach, Dewey Beach

Image: Crooked Hammock

Sunday Brunch at Crooked Hammock Brewery

This Sunday Brunch is a relaxed way to ease into the day with the Crooked Hammock flavors people already love, this time served in brunch form. 

Guests can enjoy brunch dishes, Crooked Bloody Marys, mimosa flights, and fun party drinks for the kids, making it a good option for families. 

The brewery also adds a rotating kids’ craft table or family activity each Sunday, so it is a nice pick for anyone looking for brunch that feels casual, easy, and fun for the whole crew.

• Date: Sunday, May 31st
• Hours: 10am to 2pm
• Address: 36707 Crooked Hammock Way, Lewes

Keep following the blog to stay updated on all the best events, local happenings, and things to do in Coastal Delaware.

Have any questions about our blog(s), the Coastal Delaware real estate market, or local life in our beautiful beach towns? Do you think there is something we should write about? Did you see an event coming up that we should know about? Shoot us an email at [email protected] or give us a call at (302) 212-0074. We would love to hear from you!