Portland is a long weekend destination with culinary cred, walkable charm, and easy access to coastal escapes. After two weeks of being crafty in the woods of Deer Isle at Haystack Mountain School of Crafts, I was ready to trade my rustic cabin for city comforts.
To celebrate my birthday (and cap off a few weeks in Maine), I met up with my brother and cousin for a weekend getaway dedicated to eating and drinking our way through one of New England’s most buzzy food scenes.
- Portland Itinerary At-A-Glance
- Where To Stay
- Where To Eat
- Where To Drink
- Places to Visit
- Add These To Your Portland To-Do List
Portland Itinerary At-A-Glance
- Day 1 (Friday): Lunch and whoopie pies in Freeport, Night: Drinks at Oxbow Bottling & Blending/Duckfat, Dinner at Cong Tu Bot
- Day 2 (Saturday): Day: Breakfast to go from ZU & Norimoto Bakery, Portland Head Light, Lunch at Bite Into Maine, Beers at Sacred Profane Brewery, Bissell Brothers Brewery. Evening in the Old Port – Dinner and N To Tail, Drinks at Blythe & Burrows Alleyway Speakeasy, Oxbow Bottling & Blending
- Day 3 (Sunday): Day: Lunch at Highroller Lobster Co., Portland Museum of Art, Night: Happy Hour at The Shop at by Island Creek, Dinner at Scales, Drinks at Room for Improvement
- Day 4 (Monday): Tandem Coffee, Lunch in Biddeford at Palace Diner
Where To Stay
East Bay Neighborhood. When choosing where to stay in Portland, I debated between the East Bay and the West End. While the West End is known for its charming architecture, the East Bay won out for its proximity to some of the city’s best restaurants, bars, and the Old Port.
Our Airbnb was conveniently located near Cumberland & Franklin streets and put us within a 20-minute walk of the Old Port and downtown – an easy stroll by New York standards (anything under 30 minutes is fair game). We were also a five-minute walk from Washington Avenue, home to some of Portland’s most celebrated restaurants. It was an ideal location to make the most of a weekend of eating, drinking, and exploring.
Where To Eat
Restaurants
Cong Tu Bot (Washington Avenue). I’m not typically one to seek out Vietnamese spots that don’t have the word “Pho” + a number in the name. I’ve also been spoiled by my mom’s pho – she’s (with the exception of her father, my gong gong) the best to ever do it. Cong Tu Bot is lauded as an essential Portland restaurant- and it was right around the corner from where we were staying. We couldn’t not try it.
We arrived on the later side (around 9:00 pm on a Friday) and some items had already sold out. We went with a mix of dishes: Com Chien Tom (Shrimp Fried Rice), Pho Ga (chicken pho), and Bo Luc Lac (Shaken Flat Iron Beef), plus one round of Asian-inspired cocktails.
Cong Tu Bot is a vibe—trendy and welcoming, with some seriously cool branding. More polished than your average pho joint, it did what we needed it to do.
The Highroller Lobster Co. (Old Port). Lobster rolls are quintessential Maine. If you want to have fun with your lobster roll, head to The Highroller Lobster Co. Think Johnny Rockets, but with lobster. Playful, modern retro.
I had a craving for shrimp cocktail, and Highroller delivered: plump, juicy, fancy shrimp without snobbery. The lobster roll is served on fresh, buttery brioche with chopped Romaine and 4 oz. of claw and knuckle meat. Here, it’s all about the condiments. We liked their jalapeño lime mayo (delish), but don’t overlook the curried ketchup if you’re grabbing a side of fries.
It’s all about the condiments at Highroller Lobster Co., and the curried ketchup (with fries) was one of our favorites.
We also got a corn dog (my brother can’t resist a corn dog) with a twist—Highroller’s cleverly named “Lobby Pop” features lobster instead of a beef frank.
N to Tail (Old Port). We headed into the Old Port on Saturday night for dinner but hadn’t made reservations- our bad. We first tried our luck at Miyake (Japanese), but no dice. Luckily, a friend of a friend had recommended this Korean BBQ, which was within walking distance.
We were seated right away. The multilevel layout seemed a bit random, but the service was fast, and we were ready to eat. We stuck to the classics—beef bulgogi, bibimbap, and a crispy seafood pancake. The fried eggplant appetizer was also very tasty.
Scales (Old Port). If you’re looking for top-notch seafood and a classic (yet casual) dining room atmosphere, Scales is your place. Be sure to book a table in advance. We kicked off my birthday feast with Cloverleaf rolls with garlic chive butter and cornbread with chili-honey butter. (All the butters, please.) Next came Maine mussels with Raye’s mustard.
The Baked Haddock was on the rich side, but the pan roasted Halibut with brown butter and hazelnuts shone. The wild blueberry frozen custard was delicious. I thought I’d be headed straight to bed afterward – until a friend from out of town dropped in unexpectedly and dragged us out for drinks.
The Shop by Island Creek (East Bay). Happy hour all day, every day—that’s the vibe at The Shop. Oysters are just $1.95 each if you’re dining in ($1.50 to go), making it a smart spot to indulge on briny bivalves without breaking the bank. They also offer light bites, a variety of tinned fish, and drink specials. We stopped by for an aperitif and appetizers before heading to dinner at Scales.
Happy Hour lasts all day long at The Shop by Island Creek – which means $1.95 oysters when dining in ($1.50 to-go in bundles of 6).
Palace Diner (Biddeford, ME). The legend of Palace Diner runs deep. It was recommended by both someone at craft camp as well as my New-York-turned-Portland-local friend. It’s only a 25-minute drive from Portland, making it perfectly doable as a day trip from Portland. Maine’s oldest diner has just 15 seats inside a converted rail car, making it a coveted spot for a meal. On a Monday afternoon, the wait wasn’t bad, and we snagged counter seats.
My brother and I ordered one of the last two fried chicken sandwiches of the day. (A guest who arrived after us walked out once informed they had sold out.) We also got a Deluxe Breakfast Sandwich with sausage and the famous Palace Potatoes to share.
My half of the chicken sandwich, piled with cabbage slaw, mayo, and jalapeños on a sesame bun, was already plenty. I saved my half of the breakfast sandwich for the next day (still delicious). We consumed the crispy smashed Palace Potatoes on the spot.
If I had more room, I would have gone for the cheeseburger, another menu item Palace Diner is known for. Instead, I settled for a cheeseburger fridge magnet. The swag at Palace is as solid as the food.
Food Trucks / Grab-and-Go
Banh Appetit (East Bay). We’d walked past this little shop, conveniently located right across from our Airbnb, more than once. Sure, we were on our way to lunch at Palace Diner, but with a four-and-a-half-hour drive home ahead, we’d need something for later. When it comes to banh mi, I usually choose the pork sandwich – in this case, BBQ pork (Xa Xui on the menu).
Bite Into Maine (Cape Elizabeth). Consistently ranked among the top lobster roll food trucks, we were able to try Bite Into Maine during our visit to the Portland Head Light.
Bite Into Maine offers two sizes – 4.5 oz. and 6 oz. – and six different styles of lobster roll. We split two of the larger rolls: the Maine (classic with mayo and chives) and the Picnic (a little extra, with coleslaw, butter, and celery salt), ensuring we got both a mayo-based and butter-based version. Hands down, these were our favorite lobster rolls of the trip.
Duckfat Frites Shack (East Bay). Duckfat’s Old Port restaurant is well-known, but the walk-up window at Oxbow is the move if you want to enjoy your frites with some solid craft beers. We also ordered the poutine. If you’re getting frites, I highly recommend ordering the flight of five dipping sauces. The horseradish mayo was my favorite.
Bakeries
Norimoto Bakery (Stevens Avenue, Deering) and ZU Bakery (West End). During our Portland visit, we were lucky enough to sample these two recently James Beard-awarded gems. Norimoto Bakery combines European baking techniques with Japanese sensibility and locally-sourced Maine ingredients. Zu Bakery is a micro-boulangerie with a dedicated release schedule of breads and pastries that rotates by day of week.
My early-riser cousin and his friend were kind enough to make the rounds at both spots and returned with an impressive selection of pastries for us to enjoy. All I had to do was wake up and dig in.
Where To Drink
Bissell Brothers Brewing (Thompson’s Point). Pretty sure every bachelor party in Portland had the same idea this weekend because Bissell was wall to wall bros. I grabbed a glass of farmhouse ale conditioned on spruce tips to sip on while people-watching. Bissell also serves food—we went for the wings and a mezze plate, balancing bad with good.
The Blyth & Burrows Backbar (Old Port). A friend from craft camp tipped us off to Blythe & Burrows for cocktails. It was unsurprisingly packed on a Saturday night. The host pointed us toward their first-come, first-served speakeasy, tucked down an alley behind the bar.
If you can’t get into Blyth & Burrows bar proper (Exchange St.), try your luck at their speakeasy down the alley which offers the same cocktail menu.
The speakeasy was cramped and the music was blaring. If you’re looking for a spot to bring a first date or to carry a conversation, this isn’t it. That said, the cocktails were quality.
Maine Beer Company (Freeport, Maine). Having worked in craft beer for four years, I was already familiar with Lunch, their flagship American IPA. Maine Beer Company’s reputation preceded my visit. I was surprised to find a massive, almost sterile brewpub behind its barn-like exterior, anchored by what I can only describe as a shopping mall fountain with a willow tree sculpture at its center.
No disrespect, because the beer is solid. I had the Prince Percy Pilsner and Peeper Pale Ale and we split two pizzas among us: a classic pepperoni and seasonal pizza special topped with sage and roasted butternut squash.
Before heading to Portland, we made the obligatory stop for a photo with the giant L.L. Bean Boot at the flagship store, also in Freeport. Our last stop was into Wicked Whoopies to pay respects to the official state treat: the whoopie pie.
Freeport – home to Maine Beer Company and the flagship L.L. Bean Store – is just a short 20-minute drive from Portland, making it an easy day trip.
Oxbow Blending & Bottling (East Bay). My jaw literally dropped when we rolled up to Oxbow Friday night and my buddy Austin was working the outdoor bar. I hadn’t had the chance to text him that we’d landed in Portland. He hooked us up with a round and we grabbed some fries from the Duckfat window.
Duckfat, famous for its frites, operates Frites Shack at Oxbow Blending & Bottling in the East Bay, in addition to its restaurant in the Old Port.
Oxbow became our local for the weekend. On Saturday night, DJs spun New Wave and tables were cleared from the taproom to make room for dancing. Before we left Portland, Austin hooked me up with a four-pack of black lager and a bottle of barrel-aged dark farmhouse ale. What a guy.
Sacred Profane Brewing (Now permanently closed in Portland). I’m not a hazy girl, and this spot keeps it refreshingly simple: pale lager or dark lager. That’s it. I went for the Layered—a half-liter of pale lager poured over dark lager. Unfortunately, their location in Portland has since closed but they still have a taproom in Biddeford.
Room for Improvement (Old Port). The bar that calls itself “a halfway decent bar” in their Instagram bio. I think that’s intended as an understatement. My birthday festivities continued when my friend had an unexpected layover in Portland en route to New York.
It was lively for a Sunday night around 10 P.M., and the 90s alt-rock playlist was on point. The vibe is a bit grungy in a good way, and the cocktails are solid. My friend, always the enabler, insisted we get the Flamin’ Scorpion Bowl. Standard Sunday night shenanigans.
Places to Visit
Portland Head Light. You go to Maine, you gotta visit a lighthouse. Located in Fort Williams Park, Portland Head Light been guiding ships since 1791. It’s a great spot for photos and coastal views. After snapping some pics, we headed over to the Bite Into Maine food truck for lobster rolls, then made our way to Thompson’s Point for an afternoon brewery crawl.
Portland Museum of Art (Downtown). My brother and I saw the Jeremy Frey retrospective, Woven, which had just opened Memorial Day weekend. Woven was the first major retrospective of a Wabanaki artist in a fine art museum in the U.S., showcasing over 50 stunning baskets crafted from natural materials like black ash and sweetgrass. The baskets were meticulously woven – an impressive show to catch while in town.
Add These To Your Portland To-Do List
Izakaya Minato (East Bay): Known for its ridiculously delicious Japanese food, Minato is insanely popular and tough to get into without a reservation. With all the planning and coordination required earlier in my trip, I didn’t have as much time to dive deep into Portland research or secure reservations (other than Scales). That said, thanks to the help of friends, we still managed to eat and drink very well.
Rose Foods (Oakdale). This spot north of the University of Southern Maine is about bagels and bagel sandwiches. As a New Yorker, I’m not one to seek out bagels elsewhere often. If I’m ever in the neighborhood, I’d try the Ollie Orso (salmon salad with pickled shallot) or Rivington (sable with beet and horseradish cream cheese) sandwiches.
Ramona’s (East Bay). The plan was to grab a breakfast sandwich or hoagie at this Philly-inspired sandwich shop on our last morning in Portland, right after a stop at Tandem Coffee. Unfortunately, a written sign on the door said they were closed for that day / date. Denied!
Terlingua (East Bay). Before landing at Cong Tu Bot, we tried for Terlingua, a Texas-style BBQ and taco joint recommended by a Maine-r I met at craft camp. The cocktails came recommended, but unfortunately, there was a 90+ minute wait, so we had to pass this time around.
Portland makes it easy to eat and drink well for a weekend, whether you post up downtown or venture beyond the city. Day trips to nearby towns like Freeport and Biddeford add even more to the mix, from revered historic diners to destination-worthy breweries. Having a car makes them all the more accessible. While seafood may be the regional headline, Portland’s culinary scene has range.
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