The May 15th–17th weekend has a strong mix of spring events around Coastal Delaware, from an arts festival and a strawberry festival to dog-friendly happy hour and Sunday market plans. 

This weekend is perfect for going outside, trying something new, and finding some fun things to do in the beach towns.

Yappy Hour with Brandywine Valley SPCA at Big Chill Surf Cantina

If you love dogs, want to help local rescue work, or have been thinking about getting a dog, Yappy Hour at Big Chill is a great place to go. 

The Brandywine Valley SPCA will be there with puppies that need homes, so guests can meet some cute dogs. 

The event also works as a fundraiser, with 15% of sales donated to Brandywine Valley SPCA to help cover important needs like animal food, transportation, veterinary care, spay and neuter services, and more. 

It is the kind of happy hour that gives you a reason to grab a drink, spend time with good company, and support an organization doing meaningful work for animals in need.

• Date: Friday, May 15th
• Hours: 3 pm to 6 pm
• Address: 19406 Coastal Highway, Rehoboth Beach

Image: Big Chill Surf Cantina

The Rose Levine Songbook: A Night of Living Legend! at Freddie’s Beach Bar

Freddie’s Beach Bar is bringing a true drag legend to Rehoboth for an evening of live music, storytelling, and old-school cabaret glamour. 

Rose Levine, the alter ego of Robert Levine, has been performing for more than 70 years and has been part of Cherry Grove and Fire Island drag history since 1955. 

She is also recognized by Guinness World Records as the oldest performing drag queen in the world. 

Guests can expect a well-chosen mix of Broadway classics, Jerry Herman and Stephen Sondheim songs, and her own parodies, all performed with the charm and polish of a performer who helped shape the art form. 

Freddie’s is offering a dinner-and-show format for those who want to make a full night of it, but dinner is not required to attend the performance.

• Date: Friday, May 15th
• Hours: 6 pm to 8:30 pm 
• Address: 3 South 1st Street, Rehoboth Beach

Fess Parker Wine Dinner at Bluecoast Rehoboth

The Fess Parker Wine Dinner is a summer kick-off meal with five courses from Chef Maurice and wine pairings from the Fess Parker Winery in Santa Barbara County. 

Nick Skliris from Fess Parker Winery will show guests the selections, which include estate-grown fruit from some of the best vineyards in the county. 

The menu begins with hamachi crudo served with cucumber, strawberry, fennel, citrus kosho, and shiso oil, paired with Fess Parker Riesling. 

After that, guests can enjoy pan-seared dayboat scallops with shaved asparagus, sweet corn, Parmesan, ramp vinaigrette, and prosciutto with Fess Parker Chardonnay. 

The dinner continues with under the brick quail served with sunchoke soubise, glazed baby turnips, black trumpet, and cherry jus, paired with Pinot Noir from Sta. Rita Hills, followed by venison tenderloin with root vegetable dust, carrot puree, charred broccolini, and huckleberry chimichurri matched with Parker West Pinot Noir. 

For dessert, there is chocolate torte, blackberry compote, mascarpone Chantilly, and cocoa nib crumble, all served with The Big Easy Red Blend.

• Date: Friday, May 15th
• Hours: 6 pm to 9 pm
• Address: 30115 Veterans Way, Rehoboth Beach

Tommy Conwell & The Young Rumblers at Bottle & Cork

Tommy Conwell & The Young Rumblers are bringing their Philadelphia rock-and-roll energy to Bottle & Cork, giving fans a chance to catch a band known for big, raw, and memorable live performances. 

The group first broke through in the mid-1980s, blending gritty bar-room blues with the kind of mainstream rock sound that helped them reach national attention. 

Their 1988 major-label debut, Rumble, included the Billboard Mainstream Rock hit I’m Not Your Man, and frontman Tommy Conwell became known for a stage presence that could include jumping into the crowd or playing guitar from the top of a bar. 

After reuniting and releasing Showboats and Grandstanders, their first studio album in nearly 30 years, they continue to hold their place as a beloved Philly institution with a live show that still carries plenty of punch.

• Date: Friday, May 15th
• Hours: 8 pm to 11 pm
• Address: 1807 DE-1, Dewey Beach

Intro to Gelli Printing Class at Raye of Light Studio

Raye of Light Studio's Intro to Gelli Printing is a hands-on art class for people who want to learn how to make gelli prints or get back into the process with some help. 

Beginners will learn what makes a good print, how to make a few basic pieces, and how to use new techniques to make more complex pieces. 

People who have already used a gel plate in a class can quickly review what they learned before getting creative. 

The class is all about making prints on prints, making positive and negative images, and trying out layers that can become finished art. 

By the end, everyone will have one well-developed print, other printed pieces, and a favorite picture that can be turned into art.

• Date: Friday, May 15th
• Hours: 10:30 am to 1 pm 
• Address: 117 Atlantic Ave #3F, Ocean View

Annual Strawberry Festival at Lewes Fire Dept. Station 2

The annual Strawberry Festival is back for its fourth year, bringing a full day of strawberry treats, local shopping, and family activities. 

Fifer's fresh strawberries, strawberry shortcakes, strawberry lemonade, baked goods, and other strawberry-themed treats will be available for guests. 

For those who want something extra sweet, there will also be Hopkins ice cream. 

There will be more than 75 local crafters and vendors at the Berry Market, so it's a great place to look for gifts, handmade items, and seasonal items. 

Families can also enjoy a petting zoo, a chance to touch a fire truck, a DJ, food trucks, and a visit from Grass Roots Dog Rescue. 

• Date: Saturday, May 16th
• Hours: 10 am to 3 pm
• Address: 32198 Janice Road, Lewes

Action and Advocacy Fair at Lewes Public Library

The Action and Advocacy Fair is for people who want to help their community but aren't sure where to start. 

Hosted by Women’s March Sussex, the fair brings together community members, local organizations, and advocacy groups focused on issues such as social justice, civic engagement, reentry services, public health, education, and community development. 

People who come can visit informational booths, talk directly to advocates and service providers, get useful resources, and find out how to make a difference in their own communities. 

Anyone can come to the event, whether they are new to advocacy or already involved and want to meet other people who are working for positive change. 

Guests are also asked to bring non-perishable food donations for a food drive that will help the Community Resource Center in Rehoboth.

• Date: Saturday, May 16th
• Hours: 2 pm to 4 pm
• Address: 111 Adams Avenue, Lewes

Don’t Tell Comedy in Rehoboth Beach

Don't Tell Comedy in Rehoboth Beach keeps the night a little mysterious by having a secret indoor hotel venue and a lineup that isn't revealed until the comedians go on stage.

People who buy tickets get the exact location the day of the show, which is part of the fun because the whole idea is to keep things a secret. 

The comedians are also kept secret, but each lineup is carefully put together with a mix of local talent, up-and-coming performers, and comedians who are already touring the country. 

Drinks and food will be available for purchase.

• Date: Saturday, May 16th
• Time: Doors open at 6 pm
• Location: Secret indoor hotel venue in Rehoboth 

Image: Papa Grande's

Tequila Dinner at Papa Grande’s

The Tequila Dinner brings a festive cocktail dinner to Papa Grande’s tequila room, with a four-course menu from Chef Emeley paired with tequilas from Tres Generaciones, Hornitos, and El Tesoro. 

The dinner starts with tropical tequila shrimp ceviche tostadas made with jalapeño, pineapple, and avocado crema, paired with a Kiwi Smash featuring Hornitos Cristalino Reserve, lime, agave, mint, and soda. 

The second course brings roasted mushroom queso fundido with crispy spring vegetable crudo, tortilla chips, and Tajín, served alongside a Berry Margarita made with El Tesoro Reposado, lime, agave, and mixed berry puree. 

For the main course, guests can enjoy tequila-brined roasted spatchcock chicken with cilantro salsa verde and yuca al mojo, paired with a rose water martini using Tres Generaciones Blanco. 

Dessert closes the evening with a mango mousse tartelette, fresh passion fruit, and lime-scented Chantilly cream, matched with a deconstructed spicy old-fashioned made with Hornitos Añejo Reserve, chili Reyes liqueur, and bitters.

• Date: Saturday, May 16th
• Hours: 6 pm to 9 pm
• Address: 38929 Madison Avenue, Selbyville

Rehoboth Beach Arts Festival at Grove Park

The Rehoboth Beach Arts Festival brings original artwork, local creativity, and a lively spring atmosphere to Downtown Rehoboth. 

Presented by the Rehoboth Art League and the City of Rehoboth Beach, the festival fills Grove Park with tents featuring quality work by Rehoboth Art League member artists. 

The setting adds to the experience, with the park located near the bike trail, canal dock, Visitors Center, and Rehoboth Beach Museum. 

Now in its sixth year, the event has become a popular late-spring tradition and draws thousands of visitors who come to browse art, meet artists, and enjoy one of Rehoboth’s most scenic community spaces.

• Date: Saturday, May 16th
• Hours: 10 am to 5 pm
• Address: Columbia Ave & Grove Street, Rehoboth Beach

Annual Historic Lewes Farmers Market Farm Dinner at Lewes Oyster House

The Farm Dinner at Lewes Oyster House is a unique local event that honors the farms, producers, and ingredients that make up the area's food system. 

Chef Sean Corea and his team will create a four-course menu inspired by peak-season ingredients from Historic Lewes Farmers Market farmers, giving guests a meal that is closely tied to local agriculture and the people behind it. 

There are also optional curated wine pairings, oysters available during the amuse course, a full list of wines and cocktails, and coffee from Gaia Coffee Co. 

Proceeds support the Historic Lewes Farmers Market’s mission, including food access programs for people in Sussex County.

• Date: Sunday, May 17th
• Hours: 4 pm to 9 pm
• Address: 108 2nd Street, Lewes

Melody Trucks & The Fitzkee Brothers Band with Will Bart Featuring Joe Marcinek at The Listening Booth

Melody Trucks and The Fitzkee Brothers Band are coming back to The Listening Booth for a hometown show that will be full of soulful grooves, great musicianship, and the kind of live collaboration that makes a show feel new from beginning to end. 

Joe Marcinek and Will Bart will also join the show, adding more improvisation, jam-scene energy, and musical range to the night. 

With the Fitzkee Brothers back home and sharing the stage with road-tested artists, the night is set up to feel like more than a regular concert.

• Date: Sunday, May 17th
• Hours: 6 pm to 8:30 pm
• Address: 18388 Coastal Hwy #11, Lewes

Image: The Listening Booth

Nassau Valley Vineyards Farmers’ Market

Sundays at Nassau Valley Vineyards bring together local vendors, live music, food, and locally made wine in a relaxed outdoor setting.

Guests can shop for local produce, honey, jams, arts and crafts, and other vendor goods, then stay awhile to enjoy music from artists such as 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, along with food from on-site vendors. 

Families and children are welcome, and guests can bring a chair or grab one there while they listen to music and relax with a glass of wine or sangria. 

Dogs are not allowed inside the market areas or winery buildings, but they can be walked outside those spaces or stay on leash at the picnic tables.

• Date: Sunday, May 17th
• Hours: 12 pm to 3 pm
• Address: 32165 Winery Way, Lewes

Keep following the blog for more weekend guides, local events, real estate updates, 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!