Portland, Maine Travel Guide – From a Local


Some of the questions I'm asked most frequently on Instagram is 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 absolutely love living here – it's been exciting to see it gain attention as a travel destination over the past several years. There's a reason it was chosen as Bon Appetit's Food City of 2018. Many reasons, in fact, but Portland's not just about the food (although you could easily plan an entire trip around eating your way through the city), Portland is home to a vibrant working waterfront, great small-business shopping, and an incredible art scene. It's a humble city, without pretense, qualities you could easily use to describe Mainers themselves. We don't require anything fancy – in fact, most fancy things are regarded with a high level of suspicion until we're won over. You won't find many chain retailers downtown – although a few have moved in more recently – instead, 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...

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 (fun fact: a few of those buildings and even a pier were once owned by my great-grandfather!) that are most often mentioned in travel guides. 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 what makes this city so great.

In an effort to save myself a lot of time answering future questions on Instagram (ha! But really...) below I'm sharing a few of top recommendations for what to do in Portland, Maine:

Where to eat in Portland, Maine:

Seafood:
  • Eventide: Expect to have to wait a bit for a seat at Eventide. It's worth it for a really, really good 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.
  • J's Oyster Bar: J's has been around for decades. It's right on the water, so expect to be treated to the, ahem, scent of real Maine living (hint: it's fish, get over it). This is the price you pay for incredibly fresh seafood. It's good, it's low-key, it's no-frills. And yes, most of us Mainers harbor a not-so-secret love for the smell of bait, clam flats and seaweed.
  • Highroller: Another option for fresh seafood and lobster rolls, all good, especially the fries.
  • DeMillo's: Look, I can't say I go to DeMillo's often. In fact, the last time I was there I think I was in 8th grade and it was my grandmother's birthday. BUT this floating restaurant is kind of fun in a kitchy way and I'm certainly not above some good people watching over drinks and apps. Just a heads up: it's a vibe, think sorta stodgy, somewhere you'd go for your grandma's birthday in 8th grade. Do with that what you will.
  • Harbor Fish & Free Range Fish: If you're lucky enough to be in an AirBNB or a rental 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, you'll likely see a few chefs wandering the stalls, along with plenty of locals who have the same idea.



 Breakfast & Pastries:
  • Tandem Bakery: Yes, there's always a line, but it moves quickly. Get the loaded biscuit or literally anything else, it's all so good. This is dangerously close to my apartment and I love Tandem so much. No WiFi – this is a good thing. FYI – there are two locations, the one on Congress Street has the bakery.
  • Rose Foods: Like everything else in this city, Rose Foods is extremely cute and very good. Great for bagels, 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 shutdown. 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 breakfast, and for 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 the diner to end all diners: Palace. Seriously. This place. Go during the week for the best chance at getting a seat - it's a tiny spot but the food is next level good. Like the tuna melt? When was the last time you heard a tuna melt described as life changing or ethereal? That's how good this place is.
  • LB Kitchen: Very cute and partly owned by a woman I went to college with (fun facts!), LB Kitchen makes super fresh, healthy fare that also happens to taste really good. Two locations, the one in the East End is right next to my favorite yoga studio making it the answer to where to go for breakfast after a Saturday morning class.
  • Crown Jewel: Two words: crab beignets. I finally visited this Diamond Cove brunch spot recently and am happy to report that it's very much worth the ferry ride and puzzle of figuring out your timing (for reference, we took the 10am Saturday ferry for an 11am reservation and had plenty of time). The decor is adorable, the food is delicious.



 Dinner:
  • Little Giant: We always say we're just going for drinks at Little Giant, and every time we end up eating all the food. The sister restaurant to my favorite cocktail bar, Hunt & Alpine.
  • Pai Men Miyake: Ramen. Excellent ramen. Get the Tokyo Aburra bowl... or the Pokedon bowl – or anything else on the menu. 
  • 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. A great choice if you're catching a show at the State Theater. Eat here first, rock out after.
  • Terlingua: A friend and I once got kicked out of Terlingua for chatting too long over empty glasses. I won't hold that against them – they're a popular spot, and the food is amazing. Get the burnt ends, and a good tequila drink. Rumor is they have a great brunch, too.
  • Scales: A great spot for a fancy night out or just for happy hour, Scales is more, ahem... upscale, right on the water and just beautiful. They have a great oyster happy hour, too.
  • Drifters Wife: Chris and I just went here for our anniversary and Drifters Wife lived up to the immense amount of praise it's received. Limited menu, excellent wine selection, and wonderfully low-key and laid-back for how upscale it is.



Drinks:
  • Hunt & Alpine: My favorite cocktails in all of Portland, Hunt & Alpine is owned by a couple from the other Portland (Oregon) and also serve Scandi-inspired fare. 
  • Maps: A sweet little pub located downstairs in the Old Port. Maps serves beer, wine, coffee, tea and... birthday cake. Get the cake.
  • Ruski's: A divey favorite among locals, myself included. It gets rowdy but it's usually the friendly kind of rowdy. They also serve breakfast.
  • Floods: Newly opened and owned by the same folks behind Palace Diner, Flood's also serves a tightly curated and often-changing menu. I like going here for drinks though, and we usually order the oysters or anchovies (or both) as a snack.
  • Top of the East: Surprisingly one of the only rooftop bars in the city. Top of the East is at the top of the Eastland hotel, but open to the public. Close to the State Theater.
Coffee:
  • Tandem (see above): No WiFi so don't expect to work while you're here. They make their own almond milk, 'nuff said.
  • Speckled Ax: Easy to grab & go while you're shopping or strolling Congress St., or grab a table and relax or do some work.
  • Bard: Great coffee and a great spot for working.
  • Higher Grounds: Another spot I enjoy working from, Higher Grounds is tucked away in the Old Port and also sells CBD and tinctures.


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. 
  • 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 good one. They also sell records. 
  • Print: A Book Store: Portland is unique in that it's home to more than a handful of independent bookstores located downtown. Print is one of them, and they always have a great selection of titles. 
  • 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, features everything from a specialty cheese shop to a high-end knife seller.
  • 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. 
  • Portland Trading Co.: Owned by Kazeem, arguably one of the most stylish dudes in Portland, PTC carries a variety of high-end goods + Portland and Maine-themed merch that you won't be embarrassed to wear post-vacay.

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.
  • 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.
  • 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), 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, so...
  • Take a schooner tour: This is something I did recently with my mom and it was great. The 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 Woodfords or check out South Portland, too.
  • Go see some live music: Amazing shows come through Portland, and they're usually cheaper than Boston or Providence. Check out the State Theater or who's playing down at Thompson's Point.
  • 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 (there are likely more). Go see them, they're gorgeous. A couple of favorites: diminutive Bug Light and classic Portland Headlight (shown in the first pic). 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 plenty of guides out there that will all do a better job than I, so 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 here.
  • The Press Hotel: Or here...
  • AC Hotel: Or here too.
  • airbnb: But then again, this is an option.
  • The Eastland: The one hotel in Portland I've actually stayed in, albeit a very long time ago. It's a Marriott but still very nice.

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 Portland, Maine:
  • Rockland, Maine: Check out the Farnsworth Museum, the Center for Contemporary Art, Curator Vintage, and Daughters.
  • 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), and my favorite stopover on my way North for hiking: Treats.
  • Boothbay, 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.
  • Tamworth, New Hampshire & North Conway, New Hampshire: Shameless plug: Tamworth is home to where I work, Tamworth Distilling & The Art in the Age Café. If you like craft spirits and incredible food in a bucolic, classic New England setting, take the 1.5 hour drive and visit Tamworth, which is just south of North Conway. And OK, I'll be honest, I actually don't like N. Conway that much BUT there's great hiking in the White Mountains super close by. If you go, stop by Frontside Grind for great coffee and Table & Tonic for healthy eats.



Orchid GreyMaine, Portland, Travel Guide, photography2 Comments