The first weekend of June is bringing a little bit of everything to Coastal Delaware, from outdoor markets and waterfront concerts to family-friendly festivals, theatre, food specials, and time on the water. 

Whether you want to start your morning with beach yoga, spend the afternoon browsing local vendors, or end the day with live music, dinner, or a sunset cruise, there are plenty of ways to enjoy the coast this weekend.

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: June 5th-7th
• Hours: 8am to 9am
• Address: Dickinson Avenue Beach, Dewey Beach

DAC’s West Side Creative Market in Rehoboth Beach

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, June 5th
• Hours: 5pm to 9pm
• Address: 19826 Central Street, Rehoboth 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: June 5th & 6th
• Hours: 7:30pm
• Address: 441 Old Laurel Road, Georgetown

Dogfish Head’s Bikes & Beers

Dogfish Head’s Bikes & Beers brings a full weekend of rides, brews, and good company to Milton, starting with a Fireside Chat at the Dogfish INN on Friday and continuing with the main event at the Milton Brewery on Saturday. 

You can choose from 15, 30, 45, and 62 mile routes, with registration including a commemorative pint glass, can cooler, two Dogfish Head beers for people 21 and older, marked routes, fuel stations, rest stops, mechanical support, and SAG support. 

After the ride, the party keeps going with live music, food trucks, a charity raffle, and the Milton Brewery Tasting Room & Kitchen open for food, off-centered ales, and cocktails.

• Dates: June 5th & 6th
• Various hours
• Milton Brewery address: 6 Cannery Village Center, Milton
• Dogfish INN address: 105 Savannah Road, Lewes

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: June 5th & 7th
• Hours: 9am & 10:30am
• Address: 135 Dagsworthy Street, Dewey Beach

Family Fun Fest at Coastal Wilds

This family-friendly event is all about celebrating local heroes while giving kids plenty to explore and enjoy. 

People can walk around the park, check out “Heroic Vehicles” from first responders, meet Paw Patrol and friends, take photos, and browse the Father’s Day Vendor Market for handmade items, gifts, sweet treats, and more.

There will also be food trucks, Kona Shaved Ice, face painting, gem mining, and optional add-ons like the Kangaroo Walkabout and animal encounters. 

• Date: Saturday, June 6th
• Hours: 10am to 2pm
• Address: 34215 Peppers Corner Road, Frankford

Saturday Summer Market at George H.P. Smith Park

The Saturday Summer Market at George H.P. Smith Park is a classic Lewes weekend stop and a great way to ease into the morning. 

Local vendors bring everything from fresh produce, eggs, meats, seafood, flowers, coffee, baked goods, juices, kombucha, honey, jams, pantry items, and handmade products.

You can browse favorites like Old World Breads Bakery, Gaia Coffee, Jackie Blues, The Juice Clubs, Lavender Fields, Reid Angus, Stag Run Farm, Winters Farm Florals, and more while picking up something fresh for the week, a treat for brunch, or a few local finds to take home.

• Date: Saturday, June 6th
• Hours: 8am-12pm
• Address: Johnson & Dupont Avenues, Lewes

Sangria Fest at Hudson Fields

Sangria Fest at Hudson Fields is a fun day of sipping, shopping, and family-friendly activities. 

You can purchase sangria, add your favorite fruits, and browse more than 80 local boutiques, crafters, and artisans.

There will also be food trucks, a petting zoo, and inflatables for the kids, making it an easy way to enjoy a relaxed day out at Hudson Fields.

• Date: Saturday, June 6th
• Hours: 11am to 3pm
• Address: 29977 Eagle Crest Road, Milton

Andy & Opie Kid’s Fishing Tournament at Milton Memorial Park

The Andy & Opie Kid’s Fishing Tournament is a free Milton tradition created to encourage kids and parents to spend quality time outside together. 

Kids can compete by age group, with winners chosen by the length of the largest fish caught, and there are boys’ and girls’ divisions to create more chances to win trophies and prizes. 

The event also includes bait, volunteer help with rods, face painting from CopyCat Paint Parties, free hot dogs, and Kona Ice available for purchase.

• Date: Saturday, June 6th
• Hours: 9am to 12pm
• Address: 113 Union Street, Milton

Delaware Bay Lights' Sunset Cruise in Lewes

The Sunset Cruise from Angler’s Fishing Center is a scenic way to enjoy Lewes from the water. 

The cruise travels along the Lewes-Rehoboth Canal, crosses Roosevelt Inlet, and heads into the Harbor of Refuge for views of the Delaware Breakwater East End Light and Harbor of Refuge Light. 

You won’t go inside the lighthouses, but the boat stops nearby for great views, and you can bring your own drinks, snacks, and a camera in case dolphins show up along the way.

• Date: Saturday, June 6th
• Hours: 7pm to 9pm
• Address: 217 Anglers Road, Lewes

Mid-Atlantic Sea Glass & Coastal Arts Festival at the Historic Lewes’ Main Campus

The Mid-Atlantic Sea Glass & Coastal Arts Festival brings sea glass, coastal art, music, food, and local history together at the Lewes Historical Society’s main campus. 

You can browse work from more than 75 regional and local artists, including sea glass pieces, jewelry, home decor, woodwork, metal sculpture, ceramics, photography, textiles, paintings, and more. 

The festival also includes shard identification experts from the Delmarva Antique Bottle Club, sea glass education, antique glass displays, glass-blowing demonstrations, expert presentations, live music, and food from Uncle B’s.

• Dates: June 6th & 7th
• Various hours
• Address: 110 Shipcarpenter Street, Lewes

Farmers’ Market at Nassau Valley Vineyards

Sundays at Nassau Valley Vineyards are a relaxed way to spend time outdoors with local vendors, live music, food, and locally made wine. 

You can shop for local produce, honey, jams, arts and crafts, and other vendor goods, then stay to hear music from artists like Jr. Wilson and Chatty, Matt Lafferty, Hot Sauce, Keith Mack, Ed Shockley, and more. 

Nassau Valley also has a full sangria bar made with its own wines, plus food from on-site vendors, and families are welcome to bring a chair or settle in at the vineyard for the afternoon.

• Date: Sunday, June 7th
• Hours: 12pm to 3pm
• Address: 32165 Winery Way, Lewes

Rocking The Docks at Lewes Ferry Grounds

Rocking The Docks brings The Funsters and Hot Sauce Band to the Lewes Ferry Grounds for a Fourth Street Preserve benefit show by the water. 

You can enjoy live music outdoors with bay views, sunsets, food trucks, craft brews, wine, and cocktails available on-site. 

The show is open to all ages, kids 12 and younger can attend for free, and people can bring blankets or low-back chairs for the designated seated areas.

• Date: Sunday, June 7th
• Hours: 4pm
• Address: 43 Cape Henlopen Drive, Lewes

Restaurant Week to Support the Red, White, & Blue on the Culinary Coast

Restaurant Week gives diners a chance to experience the Culinary Coast while supporting local restaurants and the Red, White, and Blue initiative. 

Restaurants throughout Coastal Delaware are participating with special menus, prix-fixe offerings, discounts, and featured dishes that highlight the region’s diverse food scene. 

Whether you're in the mood for fresh local seafood, lobster specials, steak dinners, wood-fired burgers and pizzas, craft beer pairings, or chef-created seasonal menus, there are plenty of options to explore. 

• Dates: June 7th-12th
• Various hours and addresses

Keep following the blog for more local guides, events, and things to do around 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!