If you’re looking to energize your weekend with a mix of theatrical flair, artful exhibitions, and live music, you’re in for a treat. 

Coastal Delaware is buzzing with standout events: from cult favorites on stage to creative floral displays and soulful festivals. 

Whether you’re in the mood for a night of rock, a whimsical art exhibit, or relaxed tunes by the water, this guide highlights the best local happenings to inspire your plans!

Greyhounds Reach the Beach

Dog lovers and greyhound adopters gather for this unique event celebrating retired racing greyhounds. 

Visitors can meet these gentle dogs, participate in activities, learn about adoption opportunities, as well as vendors and social gatherings for pet owners. 

It’s a heartwarming weekend that combines fun, education, and community.

• Dates: October 9th to 11th
• Location: 229 Rehoboth Ave, Rehoboth Beach
• Cost: $30 (online); $35 (at the door)

Crooktoberfest

Crooktoberfest transforms Crooked Hammock Brewery into a celebration of beer, music, and fall fun. 

Guests can enjoy live performances, seasonal brews, and hearty bites inspired by classic Oktoberfest flavors, all in a relaxed backyard atmosphere. 

The festival’s playful touches, from pretzel necklace crafting to brunch gatherings, make it the perfect mix of local charm and festive spirit. 

With its combination of great food, good beer, and live tunes, Crooktoberfest captures the laid-back Delaware fall vibe at its best.

• Dates: October 10th to 12th
• Time: Fri & Sat: 5-8pm; Sun: 10am-2pm 
• Location: 36707 Crooked Hammock Way, Lewes

SODELO — Fantasies and Fairy Tales

The Southern Delaware Orchestra brings imagination to life with Fantasies and Fairy Tales, a concert inspired by the enchanting worlds of myth and magic. 

Led by Music Director James Allen Anderson, the program features dramatic and cinematic works that transport audiences through mystical soundscapes, from dark, stormy adventures to whimsical storybook moments. 

Blending powerful orchestral performances with an atmosphere of wonder, this production celebrates storytelling magic.

• Dates: October 11th (Sussex Academy) & 12th (Cape Henlopen High School)
• Time: Starts at 3pm
• Locations: 21150 Airport Road, Georgetown & 1250 Kings Highway, Lewes
• Cost: $10-$25

Boardwalk Buddy Walk

The Boardwalk Buddy Walk is a heartwarming community tradition that raises awareness and celebrates individuals with Down syndrome. 

Families, friends, and supporters gather on the iconic Rehoboth Beach Boardwalk for an inspiring morning of unity and inclusion. 

The walk is filled with energy, smiles, and encouragement, creating a memorable experience for participants and onlookers alike. 

It’s more than just a walk, it’s a celebration of diversity and the strength of community.

• Date: Saturday, October 11th
• Time: Walk starts at 9am
• Location: Rehoboth Beach Bandstand

Image Generated by AI

Punkin Ale Fest

Celebrate all things pumpkin at Milton Brewery’s Punkin Ale Fest. 

This family- and dog-friendly event offers craft vendors, food trucks, Dogfish Head brews, exclusive seasonal libations, live music, and fall-themed games. 

From pet photo booths to a collaborative brew with a local SPCA, every corner of the festival embraces autumn fun.

• Date: Saturday, October 11th
• Time: Starts at 11am

• Location: 6 Cannery Village, Milton

Tell us which Coastal Delaware event you’re most excited about this weekend! Share your plans, and leave a comment, we love seeing how you enjoy the coast!

OktoBOARDfest!

Join the community at The Starboard for OktoBOARDfest!, an Oktoberfest-style celebration with a lively twist. 

Expect festive music, beer specials, and a cheerful crowd decked out in German-inspired attire, all set against the backdrop of Dewey Beach. 

With a relaxed, daytime vibe, it’s perfect for enjoying good company, cold drinks, and a playful take on fall festivities. 

Whether you’re coming with friends or family, this event brings beachside charm and a taste of Bavarian fun to Coastal Delaware.

• Date: Saturday, October 11th
• Time: 1 to 6pm

• Location: 2003 Coastal Highway, Rehoboth Beach

The Rocky Horror Show: LIVE at Milton Theater

Step into a world of outrageous fun and cult-classic energy as The Rocky Horror Show: LIVE returns to the Milton Theatre. 

This beloved in-house production is a local favorite, blending rock and roll, sci-fi, and cheeky humor into an unforgettable live experience. 

With its vibrant cast, dazzling performances, and infectious energy, the show invites audiences to sing, dance, and fully embrace the wild, electrifying spirit of this timeless favorite

• Various dates and times
• Location: 110 Union Street, Milton
• Cost: $32-$52

Image Generated by AI

Reefer Madness at Clear Space Theater

Get ready for a high-energy, laugh-out-loud ride with Reefer Madness, the hilariously over-the-top musical satire playing at Clear Space Theatre in Rehoboth Beach. 

Inspired by the 1936 propaganda film, the show follows clean-cut Jimmy Harper as his life spirals into absurd chaos under the influence of “Mary Jane.” 

With witty lyrics, lively jazz-inspired numbers, and sharp social satire, this cult favorite from the creators of Heathers: The Musical delivers a mix of frolic, mayhem, and irresistible humor.

• Various dates and times
• Location: 20 Baltimore Avenue, Rehoboth Beach
• Cost: $32-$52

Doors of Fame Exhibition

At the Rehoboth Art League, history and creativity come together in the Doors of Fame Exhibition. 

These iconic doors, signed by more than 285 artists, community members, and notable figures, celebrate over 85 years of artistic legacy in Delaware. 

Alongside this historic display, visitors can explore the League’s remarkable collection of mid-20th-century artworks, colonial furniture, and rare artifacts that tell the story of local artistry and cultural evolution.

• Dates: May 1, 2025–October 31, 2025
• Time: Mon-Sat: 10am-4pm; Sun: 12-4pm
• Location: 12 Dodds Lane, Rehoboth Beach

Floral Interpretations Exhibition

The Rehoboth Art League’s Floral Interpretations exhibition beautifully pairs paintings from the League’s permanent collection with floral arrangements inspired by each work. 

Created by a group of talented regional designers, including Robert Kovalcik, Ken Norman, Diane Pirkey, Emily Widdoes, and Žaneta Zubkova, the arrangements reflect each artist’s creative response through color, texture, and composition. 

Blending fine art with botanical artistry, this captivating showcase celebrates the intersection of visual and floral design, offering visitors a fresh, multisensory way to experience the League’s collection.

• Dates: September 26, 2025–October 12, 2025
• Time: Mon-Sat: 10am-4pm; Sun: 12-4pm
• Location: 12 Dodds Lane, Rehoboth Beach

Rehoboth Beach Museum's Beach Ball Gala

The Beach Ball Gala is an elegant evening that combines coastal charm with community spirit. 

Guests can enjoy fine dining, live entertainment, and dancing while supporting the preservation of local history. 

The gala is also a chance to connect with neighbors, business leaders, and supporters of the arts in a festive, upscale setting. 

As one of Rehoboth’s premier social events of the year, it’s the perfect blend of glamour and purpose.

• Dates: October 9th to 11th
• Time: Starts at 6pm
• Location: 511 Rehoboth Avenue, Rehoboth Beach
• Cost: $95-$175 

Bethany Beach Bandstand

The Bethany Beach Bandstand keeps the music alive this season with a weekend of high-energy performances. 

The Funsters bring a crowd-pleasing mix of classic rock, soul, and horn-driven hits, filling the air with danceable favorites and good vibes. 

Hot Sauce follows with its lively blend of Latin, pop, and funk influences, turning the boardwalk into a full-on beachside party. 

• Dates: October 10th & 11th
• Time: Starts at 6:30pm
• Location: 229 Rehoboth Ave, Rehoboth Beach

Schellville Fall Harvest Fest

Schellville transforms into a magical autumn wonderland during the Fall Harvest Fest, making it a must-visit for families and fall enthusiasts. 

Visitors can enjoy seasonal activities like pumpkin crafts, hayrides, and cozy treats that capture the spirit of the season. 

The vibrant decorations and family-friendly atmosphere create a picture-perfect backdrop for making memories. 

It’s one of the most festive and charming ways to welcome fall in Coastal Delaware.

• Dates: October 11th & 12th
• Time: 5 to 8pm
• Location: 36470 Seaside Outlet Drive, Rehoboth Beach
• Cost: $10 for ages 2+

ArtWalk 2025

Experience the charm of Milton during the Milton Arts Guild Art Walk! 

This annual event transforms porches and local spots into mini art galleries, showcasing the talents of local artists. 

Stroll the picturesque streets, enjoy the crisp autumn air, and discover unique works of art while exploring the historic character of downtown Milton. 

With interactive opportunities to meet the artists and learn about their creative processes, ArtWalk offers both inspiration and a personal connection to the local arts community.

• Date: Saturday, October 11th
• Time: 12-5pm

• Location: 107 Federal Street, Milton

Image Generated by AI

Grapetoberfest

Grapetoberfest is a celebration of wine, food, and family fun at Salted Vines. 

Enjoy live music, tasty bites from food trucks, and shop a variety of local artisan vendors. 

For those seeking extra fun, grape stomping adds a hands-on twist to the festivities. 

Whether you’re sampling wines, discovering unique crafts, or cheering on grape stompers, this lively, family-friendly festival captures the essence of autumn with a playful, interactive flair.

• Date: Saturday, October 11th
• Time: 11am-7pm

• Location: 32512 Blackwater Road, Frankford
• Cost: $38-$77

American Legion Craft Fair

The American Legion Craft Fair is a treasure trove of local creativity, featuring more than 50 vendors offering unique handmade goods. 

Guests can browse crafts, grab delicious food, and enjoy the vibrant atmosphere, all with free parking and a rain-or-shine guarantee. 

Beyond the shopping, the fair connects artisans and visitors while celebrating local talent and craftsmanship.

• Date: Saturday, October 11th
• Time: 10am-3pm

• Location: 113 American Legion Road, Lewes

Ashley Nicole Furio Memorial 5K Run & Crooked Crawl

Celebrate fitness, community, and giving back at the Ashley Nicole Furio Memorial 5K Run & Crooked Crawl. 

Participants can tackle the 5K course or join the fun-filled Crooked Crawl, which heads straight to a post-race party complete with music, food, and family-friendly activities. 

With a festive atmosphere that includes live entertainment and local food and beverage options, this event makes every step meaningful, supporting the Margaret H. Rollins Child Development Center and honoring the memory of Ashley Nicole Furio.

• Date: Saturday, October 11th
• Time: Starts at 9am

• Location: 36707 Crooked Hammock Way, Lewes
• Cost: $30

Tell us which Coastal Delaware event you’re most excited about this weekend! Share your plans, and leave a comment, we love seeing how you enjoy the coast!