Dogfish Head Events: May 2025
Dogfish Head Events Calendar – May 2025 | Craft Beer, Live Music, Food & More in Delaware
Get ready for an off-centered month of unforgettable fun with Dogfish Head! From epic pickleball festivals and beachy book fairs to infused beers, trivia nights, and beer-paired dinners, May 2025 at Dogfish Head is packed with unique events across Milton Brewery, Brewings & Eats, Chesapeake & Maine, and more. Whether you’re a local, a craft beer lover, or a visitor planning your Delaware beach getaway, this is your complete guide to everything happening at Dogfish Head this month.
Milton Brewery
(6 Cannery Village Center, Milton, DE 19968)
Event: Records with Randall
Date: May 1, 2025
Time: 4:30 to 6:30 pm
Details:
We’re bringing the flavor with infused beer specials and rotating DJs spinning records!! Join us and our good pal Randall the Enamel Animal the first Thursday of every month from 4:30 – 6:30 p.m. for Records with Randall. Randall is our flavor infuser that we fill with ingredients to add a new twist to our favorite beers, and we’ll have a new concoction every month for you to sip while our DJ spins.
PLUS – Every Thursday, grab a freshly-poured growler or crowler of R&D beers for 25% off! It’s also Double Points Day for our Off-Centered Society members, who will get double points on your purchases all day … that’s two points for every dollar spent! We’re sensing some rewards coming your way! Read about all of our off-season specials at
www.dogfish.com/blog/season-specials-are-back.
Event: Bingo Night
Date: May 7, 14, 21 & 28
Time: 5:30 PM to 7:30 PM
Details:
Celebrate hump day with free bingo! Come on out to the Milton Brewery every Wednesday at 5:30 p.m. for free bingo! PLUS, we’ll have $3 tacos for some game time fuel.
Event: Video Game Night
Date: May 8, 15, 22 & 29
Time: 5:00 PM to 7:00 PM
Details:
Battle it out at Video Game Night every Thursday at the Milton Brewery! Challenge other guests to a some friendly, tournament-style competition in classic video games. Registration opens at 5 p.m., and the tournament begins at 6 p.m. Registration is on a first come, first served basis, but we’ll try to make sure everyone has the chance to get in on the action!
Games will be played at our back bar, so all players must be 21+.
Event: Free Trivia
Date: May 5, 12, 19, & 26
Time: 5:00 PM to 7:00 PM
Details:
Kick-off your week with free trivia! Come on out to the Milton Brewery every Monday at 5 p.m. for free trivia! PLUS, we’ll have $3 sliders to feed your trivia munchies.
Event: Cinco De Mayo
Date: May 5
Time: 11:00 AM to 7:30 PM
Details:
We’re serving up a fiesta of flavors at our Milton Brewery for a Cinco de Mayo Celebration on Monday, May 5! Join us for some margaritas, food specials, and Micheladas made with SeaQuench and Devil Daves Bloody Mary Mix. Devil Daves will be in the house helping mix up Micheladas while sampling and giving away products for you to take home!
Food Specials:
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Chicken Tortilla Soup
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Chorizo Nachos with Beer Cheese, Pickled Jalapenos, Pico De Gallo, Sour Cream
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Pineapple Goat Cheese Guacamole with Tortilla Chips
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Beef Fajita Pizza with Peppers and Onions, Sour Cream, Roasted Tomato Salsa, Cheddar, Mozzarella, Provolone
Event: Beers & Beach Reads Book Fair with Browseabout Books
Date: May 6
Time: 4:30 PM to *:00 PM
Details:
We’re blending the best of beach season – cold beers and captivating reads – into one laid-back evening at the Milton Brewery! On Tuesday, May 6 from 4:30 – 8 p.m., we’re teaming up with our friends from Browseabout Books to bring you Beers & Beach Reads, a pop-up bookshop full of summer reads hand-picked for pairing with your favorite Dogfish Head brews.
And that’s not all! Local artist Michael Eline will be live painting onsite, turning the vibes into vibrant visuals.
What’s Brewing:
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A curated book selection from Browseabout (grab a pint, find your next read!)
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Live painting session with Michael Eline
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Coworker-curated book & beer pairings
Come thirsty for great stories, bold beers, and beachy good times!
Event: SeaQuench Slushy Release Day!
Date: May 15
Time: 11:00 AM to 8:00 PM
Details:
Summer is almost here, and so is the return of a longtime favorite…our SeaQuench Slushy! Join us at our Milton Brewery on Thursday, May 15 to kick off the summer season in coastal Delaware with this refreshing drink, plus our brand-new Tropical Squall Dole Whip!
PLUS – Stick around for Video Game Night and grab a FREE raffle ticket for your chance to win some sweet prizes that will help keep your drinks cool all summer long!!
Event: Dogfish Head PickleBrawl! Fest
Date: May 17
Time: 11:00 AM to 6:00 PM
Details:
Get ready for a day of brews, bites, and pickleball at our second annual PickleBrawl! Fest. On Saturday, May 17, from 11 a.m. – 6 p.m., we’re turning our Milton Brewery’s parking lot into a pickleball player’s paradise with the help of our friends from First State Pickleball Club.
Here’s what to expect from this Day Of Play:
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Pickleball Courts: Dive into the world of pickleball as our parking lot transforms into off-centered courts!
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Reserve: $25/hour for up to 4 players (includes 4 drink tickets for PickleBrawl! Beer).
Book at: [ticketleap link in original PDF] -
PickleBrawl! Brew: American-style lager brewed with Sorachi Ace hops, Egyptian coriander, Vietnamese Robusta black peppercorns, and more.
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Food Vendors: Uncle B’s Kitchen, Hula Bowls, Mommom’s Cheesecakes, Drizzle’s Pickles, GC Pickling Co., MF Heat Co.
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Gear: 302 Pickleball will sell paddles and apparel.
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Exhibition Match: 1 p.m. with pickleball experts!
Event: Blood Bank of Delmarva at the Milton Brewery
Date: May 20
Time: 12:00 PM to 6:00 PM
Details:
The Blood Bank of Delmarva will be at our Milton Brewery. Stop by to donate blood and receive $2 off a pint!
Register: [donate.bbd.org link in original PDF]
Brewings & Eats
(320 Rehoboth Ave, Rehoboth Beach, DE 19971)
Event: Beer “Brinner” – It’s Breakfast, for Dinner!
Date: May 2
Time: 6:00 PM to 8:30 PM
Details:
Enjoy a multi-course “brinner” paired with Dogfish Head brews. Tickets $75 (includes gratuity).
Reserve: [ticketleap link in original PDF]
MENU:
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Salmon Lox “Everything Bagel” – Potato hashbrown, cured salmon, shmear mousse, everything bagel seasoning, dill
Paired with Picklebrawl Beermosa -
Hooked Up Fried Chicken Biscuit – Boneless chicken, sausage gravy, smoked paprika
Paired with Mid-90’s Microbrewery Red Ale -
Chilaquiles – Tortillas, salsa verde, egg, corn, queso fresco
Paired with A Curious Arrangement of Stars Michelada -
French Toast – Brioche, Cinnamon Toast Crunch streusel, Cereal Milk Ice Cream
Paired with Appleflappen
Event: Benevolence Night – Overfalls Foundation
Date: May 7 & 21
Time: 4:00 PM to 9:00 PM
Details:
Support the Overfalls Foundation! 10% of proceeds benefit U.S. maritime heritage.
PLUS: Stick around for Live Band Karaoke from 8–10 PM!
Event: Live Band Karaoke
Date: May 7 & 21
Time: 8:00 PM to 10:00 PM
Details:
Sing with the Nick Kashmanian Trio every other Wednesday!
Song list: nickkashmanian.com/karaoke
Event: Locals No Meter Meet-Up
Date: May 12
Time: 4:00 PM to 9:00 PM
Details:
Celebrate the end of free parking!
Enjoy food specials, “Meter Made Shandy,” slushie cocktails, and a 7 PM raffle for swag.
Triple points for Off-Centered Society members!
Chesapeake & Maine
(316 Rehoboth Ave, Rehoboth Beach, DE 19971)
Event: Mother’s Day Lobster Sunday
Date: May 11
Time: 3:00 PM to 9:00 PM
Details:
Treat mom to 1.25 lb Maine lobsters for just $15 (sides à la carte).
Reservations: call (302) 226-3600
Event: Off the Rails with Ryan: A Hands-On Mixology Series
Date: May 21
Time: 4:30 – 6:30 PM & 7 – 9 PM
Details:
Learn to mix like a pro! Join Head Mixologist Ryan Warwick for a Rum Masterclass.
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Learn spirit history & mixology basics
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Hands-on cocktail making
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Samples + small plates
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Take-home 750ml bottle
Cost: $70/person
Limited to 20 guests per session
Off-Property
Event: SoDel Fest VIP Wine Dinner
Date: May 2
Time: 6:00 PM
Details:
Pre-festival VIP dinner ahead of the Southern Delaware Wine, Food & Music Festival on May 3.
10-course dinner featuring top local chefs, including Chesapeake & Maine’s Executive Chef Zach Dick.
Details: sodelfest.com/winedinner
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Plan Your Visit to Dogfish Head – Milton Brewery, Rehoboth Beach Restaurants & More
Don’t miss these exciting Dogfish Head events happening throughout May 2025 in coastal Delaware. With award-winning craft brews, live entertainment, seasonal food pairings, and fun experiences for locals and tourists alike, Dogfish Head is the place to be this spring.
- Discover the best craft beer events in Delaware
- Live music, karaoke, and food festivals every week
- Locations in Milton & Rehoboth Beach
Ready to sip, savor, and celebrate? Visit www.dogfish.com for more info on menus, reservations, and the full events calendar.
