Portland, Maine Travel Guide – From a Local [Updated Jan. 2024]
This lighthouse isn’t in Portland, but isn’t it nice?
Updated January 1, 2024
Some of the questions I receive most frequently on Instagram surround what to do, what to see, and where to shop in my home city of Portland, Maine. I get it – Portland is an amazing place to visit, and I love living here – it's been both exciting and nervewracking to see it gain more attention as a travel destination over the past several years. As a local and someone born and raised in Maine, I’m caught between wanting to hold it close so as not to see it change and wanting to share just how great this city is with everyone and anyone. It’s a complicated relationship. Speak to just about anyone who’s been here for any number of years and you’ll likely hear the same thing. Love for this city runs deep. Gaining popularity is a complicated matter, isn’t it?
Portland is fantastic for a lot of things, but especially the incredible food scene. Caught between the ocean and farmland, the food here is unmatched given the small size of the city proper. But Portland is not just about the food (although you could easily plan an entire trip around it). It’s home to a vibrant working waterfront, great small-business shopping, and an incredible art scene. Portland is humble, without pretense, qualities you could easily use to describe Mainers themselves. We don't need anything fancy – in fact, most fancy things are regarded with a bit of suspicion until we're won over. You won't find many chain retailers downtown – although a few have moved in more recently, much to the chagrin to many of those who’ve been here long enough to know the “Old” Portland – and the mall is laughable. But who needs a fancy mall when you have so many amazing small businesses to support? Most businesses are locally owned and frequented by the people who live just steps away. In short: Portland – and Maine in general – is awesome. Actually, it's terrible... you'll hate it... don't move here... and if you do, come in February. Kidding. Sort of. Not really.
On any given weekend, you'll find most tourists gathered in the Old Port – the charming few blocks of cobblestone streets, old brick buildings, and tiny storefronts that are most often mentioned in travel guides. (A few of those buildings and even one of the piers were once owned by my great-grandfather!) The Old Port is lovely, but it's not the only place to go in Portland. Venture beyond that small radius and you'll discover even more of what makes this city so great. bonus: You can walk just about anywhere downtown, but you will want a car if you’re flying in.
To save myself a lot of time answering future questions on Instagram (ha! But really...) below I'm sharing some of me top recommendations for what to do in Portland, Maine:
Where to Eat in Portland, Maine
Seafood, Dinner, & Drinks:
Eventide: Expect to have to wait a bit for a seat at Eventide. It's worth it for the lobster roll, and my guess is if you're visiting Portland you probably want a lobster roll, right? Of course, you do. Go here, put your name in, and wander over to Honey Paw or Hunt & Alpine for a drink or a snack while you wait for your table. Go here for: upscale but excellent seafood.
J's Oyster Bar: J's has been around for decades. It's right on the water, so expect to be treated to the scent of real Maine living (hint: it's bait and fish guts, and we can tell you’re from away based on the face you’re making). This is the price you pay for incredibly fresh seafood in this city. J’s is super low-key and no-frills – really, it’s pretty divey. Go here for: oysters and a beer.
Highroller: Another option for fresh seafood and lobster rolls, all extremely tasty. Go here for: a hipper atmosphere and a larger lobster roll that what Eventide has on offer.
The Shop by Island Creek Oysters: Super tasty and super fresh oysters and a more modern vibe than J’s. A nice option if you'd like to sit outdoors and escape tourist-congested Commercial Street in favor of tourist-congested Washington Ave. Go here for: fresh oysters, a glass of wine, and a local beer.
Luke’s Lobster: Because of Portland’s working waterfront, there aren’t as many waterfront eateries here as one might expect, and frankly, most of them aren’t that great. Luke’s is an exception. Lukes is a local chain, but it’s Maine-owned and really good - and you can’t beat the view. Go here for: tasty seafood and a view of Casco Bay.
Harbor Fish & Free Range Fish: If you're renting a place with a kitchen or grill, do yourself a favor and go for the full Maine experience – pick up some fresh seafood from Harbor Fish Market or Free Range Fish & Lobster and cook dinner at home. Better yet, stop by the Portland Farmer's Market on Saturday morning to stock up on locally-grown veggies to pair with dinner. Go here for: the local’s experience.
Hunt & Alpine: One of my favorites, and not just because I’m in love with the head chef (the head chef is Chris). H & A has been around for 10 years and during that time, they’ve won several awards and most recently have expanded their menu to include heartier fare. A great spot for cocktails or a glass of wine – or a full meal. Don’t be surprised if you see me at the bar :)
Terlingua: My favorite spot for southwestern fare in Portland. They make amazing BBQ and have great drinks. The patio during the summer is one of my favorite spots for lunch.
Crispy Gai: An amazing spot for Southeast Asian street food and cocktails to match.
Lamb’s: I love Lamb’s. This super chill bar is right on the water in South Portland and great for drinks and a snack. The food is light, so don’t expect a big dinner. I love riding my bike here in the summer.
Izakaya Minato: One of my favorite resturants in Portland and my favorite spot for a date. Serving authentic Japanese food - it’s incredible.
Pai Men Miyake: Ramen. Excellent ramen. Get the Tokyo Aburra bowl... or the Pokedon bowl – or anything else on the menu. We end up here all the time because it’s close to our place and also delicious.
Chaval: An excellent spot for a fancy date night, Chaval is the kind of place where you want to order an app, dinner, drinks, and dessert. Go all out, it's worth it. They also have a back patio.
Empire Chinese Kitchen: Chinese food, elevated. This super lively spot is always packed, but it's worth the wait.
Scales: A great spot for a fancy night out or just for happy hour, Scales is more upscale, right on the water, and just beautiful. They have a great oyster happy hour, too.
Breakfast & Cafes:
Tandem Bakery: Yes, there's always a line, but it moves generally quickly. This is in my neighborhood and I feel so lucky to have it close. FYI – there are two locations, the one on Congress Street has the bakery but both serve baked goods.
Rose Foods: Like everything else in this city, Rose Foods is extremely cute and very good. Great for bagels and incredible bagel sandwiches, a cool tote bag, and specialty foods.
Standard Baking: I once went to Standard Baking at 7am in the middle of a snowstorm when the rest of the city was entirely shut down. Somehow Standard was open (did they sleep there?), this experience only solidified my fondness for everything they make. Right across from the ferry terminal – grab a croissant or two and a cup of coffee and catch a ferry out to the islands for an A+ morning.
Miss Portland Diner: Chris and I don't do brunch, we do diner breakfast, and for diner breakfast, we always go to Miss Portland. Like a better version of your favorite greasy spoon, Miss Portland uses local ingredients for their standard diner car fare. It's good, especially after a night out or for an early pre-kayaking breakfast. Get there early and you won't have to wait.
Palace Diner (Biddeford): Portland is the kind of city where it helps to have a car, even if you're just visiting. Why? Because it's New England and a short car ride can bring you to any number of places – like Biddeford, home of Palace Diner. Go during the week for your best chance at getting a seat - it's a teeny tiny diner car but the food is next-level-good.
Bread & Friends: A new favorite for me. They serve breakfast, lunch, and dinner, along with coffee & baked goods. It’s all incredible, but the breakfast is my favorite.
Smalls: Smalls is a sweet cafe and gift shop that serves coffee drinks, locally baked cakes, and pastries, and also offers wine and a small plates menu at night. be sure to browse the shop in the back for bright and colorful gift offerings.
Bard: Bard Coffee is one of my favorite coffee shops and places to work from.
Speckled Ax: Easy to grab & go while you're shopping or strolling Congress St., or grab a table and relax or do some work.
Night Moves Bread: Night Moves is over the bridge in South Portland (about a 5-minute drive from downtown… unless the bridge is up). It’s relatively new but has quickly become a staple for us. The bread is incredible.
Where to Shop in Portland, Maine
Portland Flea For All: My favorite spot for vintage and antique home finds and the occasional jewelry or clothing score. The Flea for All is a multi-vendor shop so there's always something new. Note: As of January 2024 the FFA will be under new management and may be undergoing some changes.
Material Objects: I've been shopping at Material Objects since high school and this consignment store still has the same earnest, affordable vibe. I always find something good here.
Moody Lords: My favorite vintage store in all of Portland, a small selection but a well-curated one. They also sell records.
Little Ghost Vintage: Another great vintage spot - Little Ghost has a big selection that spans the decades and usually offers a wider size range.
Greenhand Books: Portland is unique in that it's home to more than a handful of independent bookstores. Greenhand is one of my favorites thanks to it’s amazing selection of mostly used books and great occult book selection. Prepare to get lost in the stacks and lose an hour or two.
Blanche & Mimi: The sweetest gift shop in the Old Port, I always visit Blanche & Mimi if I need a special something for someone or I'm looking for styling supplies. The vintage homewares will leave you salivating.
Longfellow Books: Another favorite bookstore that also features a great selection of used books and the occasional adoptable cat (!).
Black Boxes on Wash Ave: These shops, located in a can't-miss-it row of black shipping containers, feature rotating vendors and is an incubator for local stores to get off the ground. Most previous tenants have moved into larger spaces since occupying the boxes. There’s always something good happening here.
Pinecone & Chickadee: Looking for a souvenir that doesn't look like, well, a souvenir? Head to this locally-owned shop that features more locally-made goods plus a small selection of vintage.
Maine Surfer's Union: Forgot your swimsuit, board, or wetsuit? Just want to learn how to surf? Go here. The staff is super welcoming and incredibly friendly, and they carry a bunch of local goods, like Flowfold. Newly added: coffee and beer!
Portland Trading Co.: Owned by Kazeem, arguably one of the most stylish men in Portland, PTC carries a variety of high-end goods and Portland and Maine-themed merch that you won't be embarrassed to wear post-vacay.
Reny’s: Reny’s is… hard to describe. It’s a department store… sort of. Reny’s is a local chain and very specifically MAINE. You can find souveniers here, along with Birkenstocks, Teva’s, the best selection of Bob’s Red Mill around, discount sunglasses, factory seconds, and housewares. It’s weird and wonderful.
Zane: Located on Exchange Street in the Old Port (AKA where everyone goes when they come to Portland - it’s not undeserved, it’s very cute), Zane is where you’ll find high-to-mid-end labels, like Ganni, Le Lon Shop, Mother Denim, and Alohas.
Bonny Read: Located in the Knightville neighborhood over in South Portland, Bonney Read is another vintage homegoods favorite of mine. I’ve found so many pieces here, from vintage cookbooks for Chris, to lamps, rugs, and knicknacks. Truly dreamy.
Artemis Plus Size: Located right across the street from Bonny Read, Artemis Plus Size is a plus-specific resale boutique that offers sizes ranging from XL-5X. Chelsea also carries a variety of locally made accessories and homewares.
GoGo Refill: One of my go-to spots for sustainable and no-waste goods and locally-made home wares. It’s also a refill spot where you can refill things like laundry detergent, dish soap, etc.
What to Do in Portland, Maine
Go surfing: The Maine Surfer's Union offers group and single lessons all summer – they're super friendly. This is where I learned to surf.
Go sailing! When it comes to sailing in Portland there are a bunch of options. There’s Sail Maine, Portland Schooner Co., Sail Portland Maine, to name just a few. It all depends on what you’re looking for (some do sailing classes, while others do brunches and group charters – lots of options).
Portland Observatory: Get a view of the city from above. There are plenty of tasty spots to eat right around the Observatory, too. While you're there, walk down to East End Beach.
Go to the beach: The hardest part is choosing which beach to go to. There are plenty within driving distance and a few that you can walk to. Yes, the water is cold. Make like a true Mainer and jump in anyway, it's good for you. Ask a local or check out Google Maps to find one.
Take a ferry out on Casco Bay: The cheapest way to get a tour of the islands and learn a bit about Casco Bay? Take the mailboat out for a cruise. This ferry stops at most of the islands (not Peaks though – there’s a separate ferry for Peaks Island), and the captains usually talk a bit about each one. You can hop off on an island for the day and catch a later boat back, or just bring a cooler and cruise around while the ferry makes its stops. Peaks Island has a separate ferry. Personally, I think Peaks is overrated and overcrowded, but it's popular with tourists and it’s pretty, so...
Take a schooner tour: This is something I did recently with my mom and it was great. Portland Schooner Co. offers surprisingly affordable two-hour sails in the bay on one of its historic wooden schooners. Go for the 6PM sail for a view of the sunset – on clear days you can even see Mount Washington in New Hampshire.
Walk the city: Portland is a small city, skip the silly Duck Tours and just walk it. You can get from end to end in about 45 minutes (without stops). The outer "boroughs" are also worth exploring. Drive or take the bus (or an Uber/Lyft) over to Woodford’s Corner or check out South Portland. Honestly, though, you should rent a car.
Go see some live music: Amazing shows come through Portland, and they're usually cheaper than Boston or Providence. Check out the State Theater, Portland House of Music, or see who's playing down at Thompson's Point if you’re here in the summer.
Portland Museum of Art: Rainy day? Go see some art in the newly remodeled Portland Museum of Art.
See some lighthouses: Off the top of my head, I can think of five or six lighthouses you can get to within 20 minutes of Portland's downtown. Go see them, they're gorgeous. A couple of favorites: diminutive Bug Light and classic Portland Headlight. Also worth the drive is Nubble Light. Google it, you've probably seen pics.
Brew hop: If you're a beer fan, Portland is the city for you. There are SO MANY local breweries. I’m not a beer nerd and I don’t really drink much of it (I do make an exception for Allagash Brewing and Oxbow Brewing), so there are plenty of guides out there that will all do a better job than I, google them and drink up.
Where to Stay in Portland, Maine:
I live here, so this doesn't apply to me, but hey, here are some places to consider that I've heard rave reviews about:
The Francis: If I stayed in a hotel in Portland, I'd stay at The Francis. I love their spa, which you can read about here.
The Eastland: The one hotel in Portland I've actually stayed in, albeit a very long time ago.
Day Trips from Portland, Maine:
One of my favorite things about living back in New England – and Maine especially – is how easy it is to get to so many gorgeous locations in a relatively short amount of time. Here are a few of my favorite day trips from within a couple of hours of Portland:
Rockland, Maine: Check out the Farnsworth Museum, the Center for Contemporary Art, Curator Vintage, and Daughters.
Damariscotta: Click here for all the info.
Camden, Maine: Very cute and walkable, with great coastal hiking.
Wiscasset, Maine: Home of the very famous Red's Lobster Roll (you'll see the line before you see the shack - go across the street to Sprague’s instead), and my favorite stopover on my way North for hiking: Treats.
Boothbay Harbor, Maine: Home of the Coastal Maine Botanical Gardens.
Portsmouth, New Hampshire: Another sweet seaside village filled with great food (check out Moxy, Botanica, and Elephantine Bakery) and local shopping.