Where to Eat on Date Night or Girls’ Night Out in Freeport, Maine
There’s something special about permitting yourself to make an evening of it—good food, good conversation, and maybe even trying something new. At my recent Dabble in Oil Paint workshop, I was struck by how many guests did just that. They drove in from Harpswell, Wiscassett, and even Boothbay, and started their night with dinner in Freeport before heading to the studio. It made the whole experience feel celebratory — if coming into Freeport, why not?!
If you live in Maine, you know our towns are notorious for closing up shop early. Sometimes lights are out at 8, or even 5 or 6! But when you’re looking for a proper date night or a girls’ night out, Freeport has some great finds that keep their doors open until at least 9. Here are my five go-to recommendations:
Freeport Oyster Bar
This little spot on Maine Street has quickly become a local favorite. It’s cozy, unfussy, and all about fresh local oysters and small plates. There’s something so fun about gathering around a table, ordering a few things to share, and letting the evening unfold. It feels local and low-key, but still special— and if you don’t like oysters, don’t let that scare you away! I love their grilled cheese!
Tuscan Brick Oven Bistro
Tuscan is warm and welcoming, with wood-fired pizzas and pastas that feel like a treat. It’s the kind of place where you can order a bottle of wine, relax into conversation, and not feel rushed. Perfect for date night, but also great with a group of friends who want to linger. There’s always a good hum of energy in the room without it being overwhelming. Words of advice: make reservations ahead of time!
Antonia’s Pizzeria
Antonia’s has that casual, neighborly feel that makes it perfect for both a simple night out or a group gathering. The menu goes far beyond pizza—though their pies are definitely worth ordering. You’ll find hearty Italian dishes and generous portions.
Porters Kitchen & Bar
Porters is a newer addition to Freeport’s food scene, and it’s quickly made its mark. The atmosphere is inviting and a bit fancy feeling — begging a let’s celebrate sensation. I like that it is one of our historic buildings and hotels—- as if I am the one on a weekend getaway like our tourists and visitors.
Maine Beer Company
A short hop from Freeport’s downtown, Maine Beer Company is worth the detour. The space is airy and modern, and their beer has a well-earned reputation across the state. I love going with friends and settling in at one of their big wooden tables. It’s simple, well-known, and… invests a lot into their sustainability and solar! A win for me.
Maine may be known for early bedtimes, but when you know where to look, there are plenty of spots to stretch the night out. Pair any of these with my Dabble in Oil Paint workshop—and you’ve got yourself the perfect evening: delicious food, good company, and a memory to carry home with you.
“Next Wave” 18 × 24 (center) at Freeport Oyster Bar