Walk into The Highroller and you’re stepping into a 1950s diner that plays 90s cartoons, serves jello shots, and somehow makes this combination work perfectly with fresh Maine lobster.
The restaurant started as a food cart in 2015 with one principle: put quality food above all else, even when that seems impractical for a mobile operation.
At 104 Exchange Street in the Old Port, owner Baxter K. has built what guests call “hands down the best spot in Portland” – a retro diner experience without the downsides of actual diners, serving lobster rolls that made one California guest declare them “by far the best lobster I’ve tried in Maine.”
What Makes The Highroller Special
The restaurant operates first-come, first-served from 11am to 9pm daily, with seating that miraculously seems to always have space despite constant crowds.
The Highroller lets you customize lobster rolls through QR code ordering, choosing from options like jalapeño mayo, mango habanero, charred pineapple mayo, or traditional lobster ghee (Indian-style butter).
The retro diner vibe – complete with 90s shows playing, fresh oysters being shucked up front, funky merch shop, and that commitment to quality that started in food cart days – creates something guests describe as “fascinating” and “exceptional.”
The Story Behind the Restaurant
The Highroller launched in 2015 as a food cart where quality ingredients took precedence over convenience or cost-cutting.
That food cart foundation built a reputation strong enough to support opening a full restaurant at 104 Exchange Street, where the diner aesthetic and commitment to fresh seafood attracted lines despite no reservations policy.
The restaurant now offers full catering services from weddings to corporate events, plus pickup and delivery options, while maintaining that core principle: quality food above all else.
Food Highlights
- Lobster Roll: This earned 1,456 specific reviews – the most mentioned dish by far. Guests favor Connecticut-style with warm lobster and butter, customizable with various mayo options and served on a soft, buttery roll with slight crisp.
- Lobster Grilled Cheese: At $37, this combines two comfort food classics with 203 people specifically talking about it. One Georgia guest called it “one of the best I’ve ever had” even after the drive back to their hotel.
- Lobster Bisque: This rich soup with chunks of lobster has earned 111 mentions. One DC guest said it was “so filling, I would’ve been satisfied just eating that alone.”
- Lobster Cheese Crisp Taco: At $37, this gluten-free option uses hardened cheese as the shell – earning 28 specific mentions. The taco shell is all cheese, creating unique texture for lobster presentation.
- Surf and Turf Burger: This burger piled high with lobster has earned 60 mentions. One New York guest who added lobster ghee called it “might be my best burger ever.”
- Whoopie Pie: At $7, this traditional Maine dessert has earned 47 mentions. The New York guest called them “delectable” after trying the funky swag shop too.
Atmosphere
The Highroller sits at 104 Exchange Street in Portland’s Old Port, where the 1950s diner aesthetic meets 90s cartoons playing overhead in moderate noise levels.
Picnic tables fill the outdoor patio, while inside features bar seating, main dining room, and an oyster shucker working up front – all creating that casual, trendy, hipster vibe.
The QR code ordering system removes pressure to order everything at once, letting you add items throughout your meal while servers zip around filling drinks and food orders efficiently.
Bottom Line
Visit The Highroller Lobster because building a downtown restaurant from food cart origins in 2015 means the quality-above-all-else principle earned this reputation rather than relying on prime real estate alone.
The customizable lobster rolls with options like jalapeño mayo and mango habanero plus the lobster grilled cheese demonstrate how retro diner vibes successfully pair with fresh Maine seafood through first-come-first-served daily service.
The 90s cartoons playing alongside fresh oysters being shucked, jello shots served at a lobster restaurant, and that unwavering commitment to quality from food cart days prove this Old Port spot has earned its place as a Portland institution.
Address: The Highroller Lobster 104 Exchange Street, Portland, ME 04101
📞 (207) 536-1623
🕐 Daily: 11:00 AM – 9:00 PM (No reservations, first-come first-served)
Food cart origins 2015 | QR code ordering | Retro diner vibe | Full catering services | Funky merch shop