You’ve been meaning to make the trip to coastal Delaware. Maybe you’ve talked about it with friends, bookmarked a few things, and let it slip off the radar. Here’s your reason to stop putting it off. Dogfish Head just dropped their full 2026 events calendar – and it’s stacked. Eight major festivals, weekly live music, off-season food specials, and a brand-new dog dock diving competition that didn’t exist last year.
I pulled together every confirmed date, ticket link, and detail so you can start planning now. Whether you’re a longtime fan who makes the annual pilgrimage or someone who’s never set foot in the Milton Brewery, this is what’s worth putting on your calendar.
Valentine’s Day Celebrations – February 13 – 14
🔗 Event Details
Before the big annual festivals kick off, Dogfish Head is going all in on Valentine’s Day across its coastal Delaware locations. Brewings & Eats and Chesapeake & Maine will both host special limited menus, hand-mixed cocktails, and live acoustic sets.
Chesapeake & Maine is offering surf and turf specials with dinner service starting at 2 p.m. on Valentine’s Day. Think short rib tortellini, Maine lobster carbonara, and shareable porthole cocktails for two.
Want to make it a full weekend? The Canalside Inn is offering their “Off-Centered Occasion” package for $99 – which includes a local flower arrangement, chocolates, Dogfish Head glassware, and a voucher for a free pizza at Brewings & Eats.
302 Day Celebration – Saturday, March 7
🔗 Event Details
Named after Delaware’s only area code, 302 Day is a full-throated celebration of the First State – and it’s completely free. Dogfish Head and 302 Horseshoe Crab are teaming up once again at the Milton Brewery with live music, food trucks, local merch, and the anticipated return of the 302 Lager. That beer alone is worth the trip – a crisp American lager brewed with two-row barley malt, heirloom corn, and Sauvignon Blanc grape must.
This year, Delaware State Parks, the University of Delaware, and the Brandywine Zoo will all be on-site. Past years have featured Delaware Spirit Costume Contests, live band karaoke, and raffles benefiting Friends of Delaware State Parks. If you’ve never been, this is one of the most genuinely fun free events on the Delmarva calendar.
Weekend of Compelling Ales & Spirits (WOCAAS) – April 10 – 12
🔗 Event Details
This is the one you plan your trip around. WOCAAS is a multi-day event spanning Dogfish Head’s coastal Delaware properties, featuring experimental beers, inventive cocktails, spirit releases, food pairings, and plenty of surprises.
The main event – a self-guided tasting tour through the Milton Brewery – takes place Saturday, April 11, with events running across the full April 10 – 12 weekend. General admission tickets typically include behind-the-scenes access, 12+ food and drink pairings, and a limited-edition take-home glass. The weekend also features a Beer-Cocktail Dinner at Brewings & Eats, live music at multiple venues, and a Lobster Brunch at Chesapeake & Maine to close things out on Sunday.
Tickets sell out fast. Keep an eye on dogfish.com for release dates.
Dockfish Dogs – Saturday, May 9 (NEW for 2026!)
🔗 Event Details
This is the one everyone’s talking about. For the first time ever, Dogfish Head is hosting a dog dock diving competition at the Milton Brewery in partnership with Delmarva Dock Dogs. Picture a gigantic pool, pups launching themselves off a dock, and a variety of competitions that’ll have tails wagging all day.
You can enter your dog in the competition or just bring them along to watch. This event is free to attend and is shaping up to be one of the best additions to the Dogfish Head calendar in years. If you’ve got a water-loving pup, this is their moment.
Bikes & Beers – Saturday, June 6
🔗 Event Details & Registration
The 4th annual Bikes & Beers cycling event returns to the Milton Brewery on June 6. Choose from route options of 15, 30, 45, or 62 miles (metric century) through the scenic countryside surrounding Milton, Delaware.
Every rider gets two complimentary beers, a collectible 2026 pint glass, a koozie, and a raffle ticket for a chance to win prizes – including a brand-new bike as the top prize. The post-ride festival features live music, food trucks, and over $3,000 in raffle giveaways benefiting local cycling charities. All riding levels are welcome, and routes are fully marked with rest stops, refreshments, ride marshals, and SAG support.
Early bird pricing is live right now – $20 off registration if you sign up early. Start times sell out fast, so don’t wait on this one.
Dogfish Dash – Saturday, September 27
🔗 Event Details
Dogfish Head’s annual off-centered road race returns to the Milton Brewery. The Dogfish Dash benefits the Sussex County Land Trust, a nonprofit conservation organization dedicated to protecting natural, cultural, agricultural, and recreational resources through land preservation and education.
Past years have featured a Recycled Costume Contest and an afterparty that makes crossing the finish line even sweeter. For sponsorship inquiries, reach out to [email protected].
Punkin’ Ale Fest – Saturday, October 10
🔗 Event Details
It wouldn’t be fall without Dogfish Head’s annual tribute to their iconic Punkin Ale. This free, family-and-dog-friendly festival at the Milton Brewery celebrates the season with fall libations, local vendors, food trucks, live music, pumpkin-themed games, and plenty of Punkin Ale flowing.
A highlight every year is the partnership with the Brandywine Valley SPCA, who will be on-site with adoptable dogs. Past editions have included pumpkin decorating contests (bring your Dogfish-themed creation!), donation-based photo booths, and vendor-donated raffle prizes – all benefiting the BVSPCA. Great beer, community spirit, and a whole lot of heart. That’s this event in a nutshell.
Analog-A-Go-Go – Saturday, November 7
🔗 Event Details
Close out the year with Dogfish Head’s celebration of all things analog. On November 7, the Milton Brewery transforms into a vinyl-fueled wonderland – part music venue, part record fair, part beer festival. If you love a good beer and the warm crackle of a record player, this is your event.
Analog-A-Go-Go has become a fan-favorite tradition, drawing crowds who appreciate the brewery’s commitment to indie culture. Expect limited beer releases, an indie marketplace, and a lineup of live music that keeps the energy high all day.
Ongoing: Off-Season Specials (Through May 17)
While you’re waiting for the big events to roll around, Dogfish Head’s off-season specials are running through May 17, 2026 across Brewings & Eats, Chesapeake & Maine, and the Milton Brewery.
Here’s what’s on the weekly rotation:
- $1 Wing Days (including boneless, 6 per order)
- $12 Burger & Pizza Days with a specialty option each week
- Live Band Karaoke every other Wednesday from 8 – 10 p.m.
- Half-Price Appetizer nights
- Off-Centered Society Members Double Points Days
Check dogfish.com for the full weekly schedule at each location.
Ongoing: Live Music at Brewings & Eats
🔗 Upcoming Shows
Dogfish Head’s Rehoboth Beach brewpub keeps the stage going year-round with free live music every Friday and Saturday night. No tickets, no cover. Plus, Live Band Karaoke hits every Wednesday night – the Nick Kashmanian Trio provides the backing band while you take the mic. It’s become a staple of the Rehoboth nightlife scene.
Plan Your Stay at the Canalside Inn
🔗 Book Your Stay
If you’re making the trip for any of these events, the Canalside Inn in downtown Rehoboth Beach is a great home base. This pet-friendly boutique hotel at 34 Sixth Street has 13 rooms with canal and pool views, a swimming pool, hot tub, and kayak and paddleboard rentals right on the water. It’s a four-time Best of Delaware winner and sits about a mile from the beach and boardwalk – with restaurants and shops within walking distance. Book your stay at thecanalsideinn.com.
Stay in the Loop
Dogfish Head events sell out quickly – especially WOCAAS and the Beer-Cocktail Dinners. For the latest updates, ticket releases, and event details, visit dogfish.com/events or follow the brewery on social media (@dogfishhead on Instagram, @dogfishheadbeer on Facebook).
Here’s to another year of off-centered goodness.
