Newcomers to the Cape Region may be a little perplexed as they travel south of Rehoboth Beach and into what has become the legendary town of Dewey Beach.
What they may not know is that they have entered a zone full of charitable giving, delicious food, tasty drinks, and the backdrop for countless memories. That is, if one can actually remember being there.
“It’s home to Sand Sharks Volleyball Club, skimboard world championships, and world-class bar activities like Running of the Bull, bar Olympics, Top-8 volleyball, and the Unlock the Light Volleyball Tournament,” Jim Barnes said. “You can arrive by car or by boat, and it is a very people- and dog-friendly town. Dewey Beach is not just a place; it’s a way of life! And it’s a wonderful life with amazing sunsets!”
Barnes runs the volleyball league and has a son who is quite the player and works in town as well. Another volleyball player and Sussex Academy coach, Casey Minard, is one of the staples at The Starboard.
“I think that’s why I like this place so much; every night is so different,” Casey Minard said. “You never know what you’re gonna see or what you’re gonna run into.”
The Starboard bartender of eight seasons has witnessed quite a bit from his perch at the bar. Some moments were funny right away, while others took a little time to appreciate.
“Somebody put fireworks in the trash can on Fourth of July weekend,” Minard said.
While the culprit may have been playing with fire, they may have also warmed up to the relaxing vibe of the town along the highway.
“A big part of Dewey is this laid-back party feeling it has,” Steve “Monty” Montgomery said.
The Starboard owner cut his teeth as a bartender in town, experiencing the fraternity and sorority life that had been created in Dewey Beach before moving into the role of owning one of the most famous bars in the country.
“We’re so close to the big cities, and the fact that Dewey draws D.C., Baltimore, Philly, Wilmington, New York – it’s basically a melting pot, and that is part of what makes it so special,” Monty said.
“Dewey just feels like home away from home,” Philadelphia resident Molly Heckard said. “The people I’ve met, the experiences we’ve shared … it’s a town of solid, down-to-earth people who make you feel you belong.”
Monty, who is a fan of Washington, D.C. teams, says he enjoys mixing it up with Philadelphia fans all in the name of fun. His bar is a place where D.C. could learn a thing or two about brotherly love. It has even played host to bipartisan meals between former and current legislators like Pete Schwartzkopf, Ernie Lopez, Steve Smyk, former Governor John Carney, and current Governor Matt Meyer. They seem to leave the R and the D at the door, and for good reason.
“I don’t think there’s a town in Delaware that is this community-oriented. The businesses give back so much. Pete Schwartzkopf will tell you the whole state is nowhere close to doing what they do in Dewey,” Monty said. “I always say, let’s keep the fun in fundraising.”
The upcoming 14th Annual Dewey Goes Pink is one of the most successful fundraisers in town. Monty started it after talking with his late mom about wanting to give back more to breast cancer causes. Together, they decided on the Delaware Breast Cancer Coalition. She passed two months later, but her choice launched an event that has now surpassed $2 million over 14 years.
“We’re nothing without everybody else,” Monty said. “People say to me, you should put a Starboard in D.C., Puerto Rico, or Saint Croix, but I tell them the Starboard is what it is because of Dewey Beach and the people here.”
The town is so successful that the riches of the businesses benefit residents and landowners.
“This is the only town that I’m aware of, certainly east of the Mississippi, that has zero property taxes,” Monty said. “We can fund lifeguards, police, fire department donations, all that stuff because of the tourism, because of the parking permits, and everybody kind of gets it.”
Other notable fundraisers include the Running of the Bull and The Starboard’s annual VIP card drive, both of which raised significant support for local causes.
“Everything we do, I try to tie it back to the community,” Monty said. His staff members are on board with that same spirit.
“Part of The Starboard is being a big part of this community. We set up the beach party, cook for the lifeguards on Fourth of July, do the Christmas tree lighting and Thanksgiving, and we host the New Year’s Eve ball drop,” Monty said.
“We benefit from all that because the community is what makes us who we are,” he added. “That’s the fun part of ‘Dewey Always Wins.’”
That sense of community can be felt within local restaurants when even a wrong shipment of apples instead of oranges can create a small dilemma in the summer.
“I could call Monty right now and be like, ‘Yo. I’m out of oranges,’ and he would give me two cases, and I’d pay him back,” Lo Tibbets said. “Same with Jimmy O’Conor – we all just help each other out in that way. Whatever you need, someone has it, and they’re willing to give it. It’s not a competition. It’s more of
a community.”
Tibbets, who manages Dewey Beer Co., may not need oranges as much as The Starboard.
“On a busy weekend, it feels like tens of thousands, but I think I crushed 5,000 oranges,” Minard said.
Having each other’s backs in the hospitality business is key to cultivating a fun atmosphere across each block of the one-mile-long town.
“We try to make everything a party, and obviously, the more fun that you have, the more you’re going to want to come back,” Minard said.
Minard explained that even a simple drink order can turn into a lifelong connection.
“You grow a clientele, and some of them I see once a year, some of them I see every weekend,” Minard said. “I’ve been invited to weddings, bridal showers, baby showers, and different things.”
It’s an age-old formula Monty knows well.
“You get frustrated with some of the young college kids because they don’t tip as well, but Monty always tells us, ‘Those are the guys that are gonna get good jobs in D.C. or become lawyers and doctors. They’re your return customers year after year,’” Minard said. “We build those relationships with the Loyola kids, the UD kids, and they become customers for life.”
Love is also in the salty summer air in Dewey Beach.
“I’d say a lot of the people that are together in town now met at one bar or another in Dewey Beach,” Jay Feltz said. “I have had a couple of friends that met each other here and wound up getting married years down the road, and they’re the ones that come in here repeatedly.”
“When I think of Dewey, I think of a special kind of community, connections that go far beyond toasting to an Eagles win at Country Club,” Hailee Gooch said. “It’s celebrating our local high school state championships; it’s birthday wishes on the outside sign at Northbeach and Starboard; it’s showing up to raise money for our local fire department; it’s strangers who somehow turn into lifelong friends; it’s catching up with parents of kids I’ve coached, coaches who once taught me, and old friends I haven’t seen in a while.”
Feltz manages Dewey Beach Country Club now and says he has experienced generation after generation coming in. The same is true at Dewey Beer Co.
“Their parents brought them, and now they’re bringing their kids, or just people that stumbled upon it a couple of years ago and come back every single year,” Tibbets said. “This area is super magnetic.”
Tibbets also knows the history of the town well.
“This whole town was built around drinking, because when Rehoboth Beach went dry, the fishermen couldn’t drink within a mile of the center of town – so they came to Dewey Beach,” Tibbets said. “This whole town was based on drinking. You’re never gonna take that away from us.”
The raised blood-alcohol levels of the nocturnal crowd make for some interesting sights.
“There’s always something funny going on,” Monty said. “The funniest thing to me is when moms, dads, or grandparents are in here at like six or seven o’clock in the evening having their crushes and are like, I gotta get out of here! My kids are coming at eight, and they told me it’s their place.”
Minard has his own favorite observation.
“One of the best things is that slider we have that separates the bar area from the dining room,” Minard said. “You’ll have a family sitting there at eight o’clock at night, eating dinner with grandma and grandpa, and just on the other side of the slider there’s a couple making out up against the glass.”
But nighttime isn’t the only time for stories. On one St. Patrick’s Day, a legend was born at Dewey Beer Co. – the “mashed potatoes girl.”
“It was an older guy, his wife, and their friend. The wife and friend went to the bathroom, and the guy was just sitting there. Their plates were still there, but they were done,” Tibbets said. “This girl, intoxicated, sits down with the gentleman and starts eating the mashed potatoes. He’s laughing, the table behind him is laughing, so it was a carefree moment.”
“I walked up to her to tell her that those weren’t hers, and all you see are all six of her friends recording outside of the building,” Tibbets said. “I said, ‘Hey, that’s not your food.’ She said, ‘I ordered this inside here.’ I said, ‘You didn’t.’ She said, ‘I’m sorry I didn’t.’”
Employees at Dewey Beer Co. would love to know the identity of the mashed potatoes girl, but no one has claimed the spud award.
Feltz has seen some things himself.
“I’ve seen a lot of crazy things over the years, whether it’s people getting too out of hand, having too much to drink, getting arrested, or people just having too much fun,” Feltz said. “Maybe passing out on the street corners, or maybe going into the wrong house at the end of the night.”
While it may generate laughs, in the end, everyone just wants everybody to love everybody.
“Sometimes they come in the next morning, and they completely forget that they passed out on my front doorstep,” Feltz said. “You’re like, ‘You remember, you passed out here last night?’ They’re like, oh my God, did I do anything wrong?”
There are times, however, when the humor of a prank takes center stage. Take Woody’s, for instance, and Jimmy O’Conor’s world-famous crab cakes. I personally have family from the Philadelphia area who trade in their cheesesteaks for what they consider the best crab cake in the world when they visit. Little did they know that some people in Dewey are just trying to give them away.
“On April Fool’s Day, I always put ‘Free Woody’s crab cakes’ on the marquee,” Monty said.
While the crab cakes are celebrities themselves, Dewey has also attracted its fair share of real ones. People may know Ryan Phillippe, but Denzel Washington and Sandra Bullock both frequent The Starboard. In fact, Owen Wilson and Vince Vaughn were once turned away at the door because Monty didn’t realize they were the Wedding Crashers stars. He was applauded for treating them like everyone else.
“Scott Van Pelt, a buddy of mine, is in here all the time,” Monty said.
Philadelphia Eagles tight end Dallas Goedert, along with Avonte Maddox and Minnesota Vikings tackle Brian O’Neill, once hung out at The Starboard disguised in staff shirts, checking IDs for fun.
While Dewey Beach can get the best of folks, it also shares its winnings. The Starboard was recently named one of the best 29 bars in the country by USA Today, and its cross-street neighbor brews up success too.
“We won best brewpub in Delaware two years ago; we were third this year, which is awesome,” Scotty Bunting said. “Our beer is amazing. I may be biased, but it’s just a cool place with good food and good beer, and people gravitate toward that, which
is awesome.”
Dewey Beer Co. is looking forward to what locals call the “Local’s Summer,” which runs into November and is a favorite time of year.
“As locals … Dewey is More Gooder!” Josette Castiglione said. “Best bartenders in the area, you are guaranteed to run into friends from every chapter of life. The energy is unmatched. Something is always going on. The off-season is the BEST!!”
Whether it’s the staple restaurant The Starboard, a classic like Gary’s Dewey Beach Grill, the always-packed Woody’s, the decade-old Dewey Beer Co., or the hidden gem Dewey Beach Country Club, everyone finds their way to a win before Dewey Beach ultimately pulls out the victory – just as it has for generations.
