The last weekend of September in Coastal Delaware is packed with cultural festivals, live performances, food and drink events, and family-friendly activities.
Whether you’re interested in literature, local history, live music, or coastal cuisine, there’s something for everyone to enjoy.
Take a look at what’s happening from Friday, September 26th through Sunday, September 28th:
Negroni Week at Chesapeake & Maine
Celebrate Negroni Week at Chesapeake & Maine, where this iconic Italian cocktail gets the spotlight it deserves.
Enjoy four handcrafted Negroni creations, each with its own distinctive twist: the classic, espresso-inspired, smoky Swashbuckler, and the autumnal Harvest.
Perfect for sipping with friends or discovering new flavors, the event offers a bold, bitter, and beautifully balanced toast to this beloved cocktail.
With expert preparation and creative combinations, Chesapeake & Maine makes Negroni Week a must-visit for cocktail enthusiasts.
- Dates: September 24th-28th
- Time: While the restaurant is open
- Location: 316 Rehoboth Avenue, Rehoboth Beach
9th Annual History Book Festival
The History Book Festival is a highlight of the season in Lewes, drawing book lovers from across the region for a celebration of stories that bring the past to life.
This unique literary event invites nationally recognized authors to share their work, offering readers the chance to engage in thoughtful conversations, attend panel discussions, and discover new perspectives on history.
With events spread across multiple venues, it creates a lively atmosphere throughout town and makes Lewes feel like a hub for ideas and dialogue.
The Saturday presentations are especially packed with opportunities to hear from a wide variety of voices, making it a must for anyone passionate about books and history.
- Dates: September 26th-28th
- Various locations across Lewes
- Check out the Saturday Presentations Schedule
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Milton Theatre Events
Milton Theatre’s weekend lineup offers something for every taste in live performance.
Kicking off the weekend, Kategory 5 delivers a powerhouse tribute to the classic rock era, performing challenging hits from Yes, Styx, Rush, Boston, and Kansas with precision and energy that will thrill longtime fans.
The following night, Smokus Pocus takes the stage with a 420-themed magic show, blending mind-bending illusions and humor in an unforgettable adult-oriented experience.
Closing out the weekend, internationally acclaimed violinist Andrew Sords captivates audiences with his expressive performances and flawless technique, performing both solo and chamber works that highlight his global reputation and artistry.
- Dates: September 26th-28th
- Location: 110 Union Street, Milton
- Times and prices vary by event
Purple Parrot
The Purple Parrot is Rehoboth Beach’s go-to spot for nightlife and live entertainment.
This adults-only biergarten offers a rotating weekend of fun, from high-energy karaoke on Friday and Saturday to the wildly entertaining Birdcage Drag Show on Sunday.
With its casual outdoor setup, vibrant atmosphere, and focus on community fun, the Purple Parrot provides the perfect place to kick back, sing along, laugh, and experience a lively slice of local beach culture.
- Dates: September 26th-28th
- Time: 9pm
- Location: 134 Rehoboth Avenue, Rehoboth Beach
Dewey’s Golden Jubilee
Dewey’s Golden Jubilee is a weekend celebration for Golden Retriever lovers and their furry friends, blending fun, community, and a great cause.
Attendees can enjoy the relaxed beach atmosphere while connecting with other Golden families, letting their dogs romp on the sand, chase tennis balls, and swim in the surf.
The event also features a Friday night parade through Rehoboth and a beach bonfire on Saturday evening, creating a joyful, social experience for both pets and humans.
In addition to the festivities, the Jubilee supports the Morris Foundation’s Golden Retriever Lifetime Study, one of the largest and most comprehensive canine health studies in the U.S., collecting valuable data to help improve the lives of dogs everywhere.
- Dates: September 26th-28th
- Location: Dewey Beach & Rehoboth Beach
- Check out their full schedule
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Bethany Beach Bandstand
The Bethany Beach Bandstand is bringing back the ultimate ‘80s experience with two nights of high-energy tribute bands.
On the first night, The Jimmies ‘80s Flashback Band will transport you to the era of big hair, neon colors, and unforgettable hits, covering classic tunes from Bruce Springsteen, Tom Petty, Queen, and Aerosmith.
Their electrifying performances and authentic sound make it impossible not to dance and sing along.
The following night, Separate Ways the Band delivers a meticulously accurate tribute to Journey, recreating the early-to-mid ‘80s lineup with spot-on vocals, harmonies, and visual flair.
Known as “the next best thing to Journey,” this nationally-touring act promises an unforgettable evening for classic rock fans of all ages.
- Dates: September 26th & 27th
- Time: 6:30pm
- Location: Boardwalk, Bethany Beach
Arena’s Deli & Bar
Arena’s Riverside stage comes alive with high-energy performances that keep audiences returning for more.
Bucket of Hot delivers a thrilling set packed with genre-blurring medleys, mixing radio hits, deep cuts, and fan favorites from their catalog of over 600 songs.
Following that, Freshly Squeezed, a female-fronted party band, keeps the dance floor moving with a bold blend of rock, pop, dance, reggae, ska, classic rock, and ‘80s hits.
With guitar-driven grooves and powerhouse vocals, both nights at Arena’s offer unforgettable music, infectious energy, and a true celebration of live performance.
- Dates: September 26th & 27th
- Time: 9pm
- Location: 200 NE Front Street, Milford
The Room at Cedar Grove
Enjoy an intimate evening of live music and dinner at The Room at Cedar Grove.
The Elwood Bishop Funky Groove Project kicks things off with a high-energy mix of funk, blues, and jazz, featuring vibraphonist Joe Baione and a tight, dynamic ensemble.
The next night, Eric Andersen celebrates the release of his new album “Dance of Love and Death”, performing selections from the album and his long, celebrated career in folk music.
Both nights promise unforgettable performances in a cozy, welcoming setting.
- Dates: September 26th & 27th
- Time: 6:30-8:30pm
- Location: 32882 Cedar Grove Road, Lewes
- Cost: $52-$61 (includes dinner)
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Nalu Surf Bar & Grill
Nalu Surf Bar & Grill in Dewey Beach offers lively, beachside entertainment with back-to-back nights of fantastic live music.
Matt Quinton kicks off the weekend with a high-energy set, setting the stage for fun and dancing, while Decade 80 brings a nostalgic throwback vibe, performing beloved hits that keep the crowd singing along.
With its surf-inspired décor, casual atmosphere, and infectious energy, Nalu is the perfect place to enjoy music, good drinks, and a lively coastal night out.
- Dates: September 26th & 27th
- Times: 7-11pm (Friday); 8-11pm (Saturday)
- Location: 1308 Coastal Highway, Dewey Beach
Blue Moon Spotlight Show
The Blue Moon Spotlight Show is a long-running favorite for live drag entertainment in Rehoboth Beach.
Known as the best drag show at the beach for over 20 years, this single evening event delivers bold, theatrical performances with incredible costumes, dazzling choreography, and plenty of laughs.
For those looking to combine dinner with the show, select “high top” seating in the Atrium for an up-close experience, making it an evening of glamour, fun, and unforgettable entertainment.
- Date: Friday, September 26th
- Time: 9pm
- Location: 35 Baltimore Avenue, Rehoboth Beach
Fresh Art Fridays – Brittney Bodner
Fresh Art Fridays presents Brittney Bodner’s “Seven Elements of Art,” an engaging visual arts experience exploring line, shape, form, space, value, color, and texture.
Each work is a playful reimagining of these fundamentals, brought to life through an experimental and intuitive process.
Guests can immerse themselves in a vibrant journey of imagination and emotion, observing art that celebrates curiosity and creative exploration.
Brittney’s Austrian-American background and lifelong immersion in art inform her joyful, whimsical, and colorful approach, making this exhibition a feast for the eyes and the spirit.
- Date: Friday, September 26th
- Time: 5-9pm
- Location: 37401 Malloy Street, Rehoboth Beach
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Lightship Overfalls Gala
The Lightship Overfalls Gala is a premier fundraiser supporting the preservation of Delaware’s only maritime museum and National Historic Landmark.
This year’s “Float The Boat” theme directly benefits the ship’s upcoming winter maintenance and ongoing educational programs.
Guests can enjoy a festive evening of mingling, cocktails, dinner, live music from 33 1/3 The Band, dancing, and incredible raffle prizes and a live auction, all set against beautiful bay views.
It’s a night of merriment for a good cause, offering a blend of entertainment, community spirit, and support for an iconic piece of Delaware history.
- Date: Friday, September 26th
- Time: 6-9pm
- Location: 2701 Cedar Street, Lewes
- Cost: $125
3rd Annual 86 Hook & Ladder Brewfest
The 86 Hook & Ladder Brewfest is a celebration of craft beer, live music, and community spirit, all in support of the Rehoboth Beach Volunteer Fire Company.
Sample beers from over a dozen Delaware-area breweries, enjoy bites from local food vendors, and check out unique offerings from a variety of on-site vendors.
With music keeping the energy lively, attendees can cast votes for Best in Brew, Best IPA, and Best Beard while sipping on bourbon, moonshine, and craft brews courtesy of the event’s title sponsor, Atlantic Liquors.
Beyond the fun, the festival raises crucial funds to support life-saving fire equipment and services for the community, making every pint a way to give back.
- Date: Saturday, September 27th
- Time: 12-4pm
- Location: 229 Rehoboth Avenue, Rehoboth Beach
- Cost: $21.50
Lyn McDonald — When The Walls Came Down
Join author Lyn McDonald at Browseabout Books for a book signing of When The Walls Came Down.
Follow Mouse on a heartfelt journey of self-discovery as he navigates life, learns to listen to his own heart, and lets go of what no longer serves him.
This event offers fans an opportunity to meet the author, get their copies signed, and explore the world of Mouse in an intimate, engaging setting.
- Date: Saturday, September 27th
- Time: 11am-1pm
- Location: 133 Rehoboth Avenue, Rehoboth Beach
Dimitra Yoga Classes
Dimitra Yoga’s Saturday lineup offers two distinct ways to deepen your practice.
Start the morning with a 75-minute Vinyasa 2 class led by Abby Spooner, an intermediate-level heated session (80–85°) designed to ignite inner fire and guide students through dynamic, flowing sequences.
Following that, Lisa Wise leads Hatha 1, a 60-minute all-levels class at a gentler pace, ideal for new students or anyone seeking a grounding, non-heated practice with clear and safe instruction.
- Date: Saturday, September 27th
- Location: 17437 Ocean One Plaza, Ste 1, Lewes (also available online)
- Times: 9:30-10:45am (Vinyasa 2); 11am-12pm (Hatha 1)
- Cost: $35
Coastal Delaware Artisan Market
The Coastal Delaware Artisan Market is a vibrant showcase of local creativity, bringing together talented artists and makers to display and sell their one-of-a-kind handmade treasures.
From intricate layered art and hand-crafted jewelry to unique ceramics, stained glass, wearable art, and holiday décor, there’s something for every taste.
Guests can meet the artists, browse the stunning array of fine crafts, and even get a head start on holiday shopping in a relaxed, stylish setting at the Cambria Hotel.
With live music and complimentary parking, it’s a perfect day to discover unique gifts, support local talent, and soak in the beauty of the season.
- Date: Sunday, September 28th
- Time: 11am-3pm
- Location: 17222 Hood Road, Rehoboth Beach
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Nassau Valley Vineyards Farmers Market
The Nassau Valley Vineyards Farmers’ Market is a beloved Sunday tradition, offering a mix of local produce, artisanal goods, and live music in a relaxed, family-friendly atmosphere.
Guests can browse fresh fruits, honey, jams, crafts, and more while enjoying performances from talented regional musicians.
With a full sangria bar featuring Nassau’s own wines and plenty of seating to kick back and enjoy the tunes, it’s a great way to spend an afternoon soaking in the vineyard’s charm.
The market is welcoming to families and a perfect spot to combine shopping, music, and local flavors for a true Coastal Delaware experience.
- Date: Sunday, September 28th
- Time: 12-3pm
- Location: 32165 Winery Way, Lewes
Spooky Bookish Earring Workshop with Sabina of Bookish Designs
Get crafty this fall at the Spooky Bookish Earring Workshop with Sabina of Bookish Designs.
Participants will create their own pair of themed earrings (choose from pumpkins, coffins, witches, and more) using polymer clay and a full set of tools and materials provided.
Sabina guides attendees step by step, from shaping and assembling to detailing and finishing, making it perfect for beginners.
Enjoy a fun, creative session with the option to wait during baking or pick up your earrings the next day.
- Date: Sunday, September 28th
- Time: 11am-1pm
- Location: 17689 Coastal Highway, Lewes
- Cost: $55
Which of these events are you planning to check out? Share your plans in the comments, and stay tuned to our blog for more updates on what’s happening around Coastal Delaware!