You walk down Exchange Street in Portland, Maine, and you see the line. It’s almost always there. A swarm of people standing outside a storefront with a bright red-and-white aesthetic that feels more like a 1950s diner had a baby with a streetwear brand than a traditional New England fish shack. This is The Highroller Lobster Co., and if you’ve spent any time on food TikTok or Instagram, you’ve definitely seen their neon signs and brioche buns.
But here’s the thing. Most people think it’s just a "tourist trap" because it’s loud, flashy, and expensive. Portland is a serious food town. We’re talking about the city that boasts Eventide, Duckfat, and Fore Street. In a place with that much culinary street cred, a spot that leans heavily into branding usually gets a side-eye from the locals.
Honestly? They’re wrong.
The Highroller Lobster Co. isn’t just a gimmick. It’s a masterclass in how to take a stagnant, "sacred" regional dish—the lobster roll—and actually make it interesting again without ruining the integrity of the crustacean. It’s messy. It’s chaotic. It’s arguably the most fun you can have with a buttered bun in the Northeast.
How a Food Cart Broke the Lobster Roll Rules
Before it was a brick-and-mortar powerhouse, Highroller started as a mobile food cart in 2015. The founders, Andy Gendron and Baxter Key, weren't trying to replicate the classic "mayo or butter" debate that has bored Maine travelers for decades. They wanted something that felt like a party.
Most lobster rolls in Maine follow a strict code of ethics. You have the "Maine Style," which is cold lobster tossed in a tiny bit of mayo, usually on a toasted split-top bun. Then you have the "Connecticut Style," which is warm lobster drenched in butter. That's it. Those are the rules. If you deviate, people get weirdly protective.
Highroller didn't just deviate; they blew the doors off.
They started offering sauces that made purists cringe. Jalapeño mayo. Black garlic mayo. Lime mayo. Roasted pineapple mayo. It sounds like sacrilege until you actually bite into it. The sweetness of fresh Maine lobster—which they source meticulously—actually holds up incredibly well to acidity and heat. By the time they moved into their permanent space at 104 Exchange St in 2017, they had already built a cult following that didn't care about "tradition." They cared about flavor profiles that didn't put them to sleep.
What You’re Actually Ordering (And What to Avoid)
If you’re going to The Highroller Lobster Co., you need a strategy. The menu is deceptively simple but can get overwhelming if you're trying to customize everything.
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The Lobster Roll
This is the flagship. It’s a four-ounce pour of fresh meat. The brioche bun is made specifically for them by Southside Bakery. It’s thick. It’s sturdy. It has to be, because the amount of butter they use would disintegrate a standard grocery store bun in seconds. You pick your sauce. If it’s your first time, go with the Charred Pineapple mayo or the Lime mayo. The acidity cuts the fat of the lobster and the buttered bread in a way that regular mayo just can't.
The Lobby Pop
Basically a lobster tail on a stick, battered and fried. Is it necessary? No. Is it delicious? Yes. It’s the kind of thing you buy because you’re on vacation and you’ve already decided that cholesterol is a problem for "Future You."
The Burger
Surprisingly, their burger is one of the best in Portland. They use a blend from W.A. Bean & Sons (a legendary Maine butcher) and top it with brisket. But the real pro move? The "Surf & Turf." You get the burger and add lobster meat on top. It’s a $30+ sandwich, but it’s a core memory.
The Fries
Get the Old Bay fries. Don’t overthink it. They’re salty, crispy, and serve as the perfect vessel for whatever extra sauce is dripping off your roll.
The "Vibe" and Why It Matters for Business
The Highroller Lobster Co. succeeded because they understood something other Maine eateries missed: the demographic shift in travel.
Millennials and Gen Z travelers aren't always looking for the quiet, salt-crusted wharf experience. They want high-energy environments. Highroller feels like a clubhouse. There’s loud music, a curated selection of local craft beers (Bissell Brothers and Maine Beer Co. are usually staples on their tap list), and a merchandise line that sells out as fast as the food.
They turned a meal into an "event."
From a business perspective, they’ve also mastered the art of the collaboration. They do "takeovers" and limited-run items with other local legends. This keeps the local crowd coming back even when the cruise ships aren't in port. They’ve managed to bridge the gap between "tourist destination" and "local hangout," which is the Holy Grail for any restaurant in a seasonal city like Portland.
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Addressing the Price Point
Let’s be real. Eating here is expensive.
Market price for lobster is volatile. In 2026, those prices aren't getting any lower. You can easily spend $100 for two people if you're getting rolls, sides, and a couple of local IPAs.
Is it worth it?
If you want the "authentic" experience of sitting on a wooden bench at a lobster pound while seagulls try to steal your food, go to Portland Lobster Co. or head out to Cape Elizabeth for the Lobster Shack at Two Lights. Those places are great. They are beautiful.
But if you want a lobster roll that actually tastes like a chef-driven dish rather than just a commodity, Highroller is the spot. You're paying for the quality of the brioche, the complexity of the house-made sauces, and the fact that you’re in the heart of the Old Port.
The Logistics: How to Actually Eat There Without Losing Your Mind
If you show up at 1:00 PM on a Saturday in July, you’re going to have a bad time. The wait will be over an hour.
Instead, try these three things:
- Go for "Linner": Between 3:00 PM and 4:30 PM is the sweet spot. The lunch rush has cleared out, and the dinner crowd hasn't started drinking yet.
- Order Online: You can skip the line entirely by ordering for pickup. Take your bag down to the waterfront (it’s a five-minute walk) and eat on a pier. It’s a better view anyway.
- Check the Merch First: If the restaurant is packed, the merch side is usually a bit quieter. It gives you a chance to see the vibe before you commit to the wait.
Common Misconceptions About Highroller
People love to hate on things that are popular. You’ll hear locals say it’s "overrated" or "all branding."
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That’s usually a sign that they haven't eaten there in three years.
The quality control at The Highroller Lobster Co. is actually surprisingly tight. Because they move so much volume, the lobster is incredibly fresh. It doesn't sit around. The buns are toasted to order. The sauces are made in-house.
Another misconception is that it’s "not real Maine food." Maine food is evolving. It’s not just boiled potatoes and steamed clams anymore. The state’s food scene is defined by innovation and an obsession with local sourcing. Highroller fits that definition perfectly. They use Maine lobster, Maine potatoes, Maine buns, and Maine beer. They just put a red-and-white sticker on it and turned the volume up to eleven.
Making the Most of Your Visit
When you finally get your hands on that roll, don't just inhale it. Look at the construction. The way they nestle the meat into the bun ensures you get a piece of claw and tail in almost every bite.
Pro Tip: Ask for a side of the "Lobby Butter." It’s basically their clarified butter infused with lobster shells. Dipping your fries in that is a life-changing experience.
Also, don't sleep on the "Milkshakes." They aren't always on the menu, but when they do collaborations with local creameries, they are elite.
Actionable Insights for Your Trip
- Parking is a nightmare: Don't even try to park on Exchange Street. Use the Fore Street Garage or the Custom House Wharf lot. It’ll save you twenty minutes of circling blocks.
- The "Flight" Option: If you're with a group, get a few rolls with different sauces and cut them in half. Sharing is the only way to try the black garlic and the jalapeño without buying two full meals.
- Drink Local: They always have the best of Maine's beer scene on tap. If you see something from Belleflower or Oxbow, get it. Those breweries are doing world-class work that pairs perfectly with seafood.
- Budgeting: Expect to pay around $35-$45 per person for a full meal including a drink and tip. It’s a splurge, so treat it like one.
At the end of the day, The Highroller Lobster Co. is a testament to what happens when you take a traditional product and apply a modern sensibility to it. It’s loud, it’s vibrant, and it’s unapologetically Maine. Whether you’re a purist or a thrill-seeker, it’s a foundational part of the modern Portland food story. Just make sure you bring an appetite and maybe a bib. You're going to need it.