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If I spent a weekend in Portland, Maine
here's what I would do. the bonus newsletter of the month.
When someone tells me they are coming to visit Portland, my initial reaction is confounding, even to me. I instantly am struck with jealousy - which makes zero sense, obviously, I live here.
As this newsletter is being sent, I am currently in the other Portland. We are on a Pacific Northwest crawl - beginning in Portland, Oregon, winery cruising through Willamette Valley, hiking along the coast near Cannon Beach, and finally landing in Seattle. I’m on vacation - and vacation me, bright-eyed and bushy-tailed Chelsea, is different than every day me.
So, vacations in my Portland fill me with jealousy! I want to vacation in Portland! I want to be carefree for an extended stay and eat/drink everything I can get my hands on (because calories/indigestion/money isn’t a real thing on vacation!) I don’t want to do real life - I want to fill my days with whatever looks and sounds good!
And maybe that’s why - after, oh, I don’t know, 6,000 requests for what to do in Portland from friends/family/strangers on vacation over the years - I’ve never just put together a freaking Google Doc with my top picks. I’m jealous, alright!
But here we are. I’m doing it. And, turns out, people really just want a listicle from time to time and I’m happy to be of service.
If I were here for a quick 48 hour getaway, here’s what I would do. With that said, this task is impossible. I could make this 100 times over and still not be satisfied - because if it’s not apparent enough, I love it here. So, despite my ability to supply you with enough recommendations to last you a full month’s stay, we have to start somewhere.
Here are three separate itineraries - totally interchangeable but conscious of weather & one suitable for kiddos - perfect for a Summer or Fall getaway to Portland, Maine.
If you are visiting Portland soon: enjoy!!
If you are local to Maine/Portland: this is my Portland google doc! save, share & send this to all of your inquiring visitors!
PS: this newsletter’s comments are open to all! Tell me your favorite must-do Portland spots!
Itinerary #1 (perfect weather)
🔸Pre-Dinner: The Shop by Island Creek Oysters
Get in the Maine spirit and throw back a few oysters (and drinks) on their beautiful patio.
🔸Dinner: Izakaya Minato
I think this restaurant expertly illustrates Portland’s prowess when it comes to food - plus it’s priced extremely reasonably. Get the daily tempura, garlic edamame, JFC & everything else.
🔸Nightcaps: Maine Craft Distilling & Cocktail Mary
Both around the corner & walkable from dinner, Maine Craft Distilling often has live music on Friday nights and Cocktail Mary, a queer craft cocktail bar, is always a blast.
🔸Breakfast: Bread & Friends
I have yet to try something here I don’t like. Grab & go from their pastry counter, or sit down to enjoy dishes like their soft scrambled eggs with caramelized onion jam & seeded sourdough.
🔸Activity #1: Pick a Beach
Set-up shop & swim or just beach comb! Here are some favorites close to Portland: Kettle Cove (find the secret beach!), Crescent Beach (soft sand - a rarity!), Ferry Beach State Park
Reserve a table in their expansive outdoor margarita garden! I dream about their Terlingua Salad (with tons of smoked brisket on top - because, priorities.)
🔸Activity #2: Wine Sail with Wine Wise
Departing from the Maine State Pier, hop aboard the 74-foot sailboat, the Frances, and enjoy wine while you take in the sights. Afternoon cruises available!
→ Prefer to stay on land? Head to this fun pocket of breweries next to each other: Belleflower Brewing, Goodfire Brewing, Lone Pine Brewing, Hi-Fidelity, Après (hard seltzers)
→ Want to skip drinking? Book a kayak tour with Portland Paddle! For a unique Maine experience: rent a kayak and explore Richmond Island.
🔸Dinner: The Well at Jordan’s Farm (Cape Elizabeth)
This reservation needs to be made well in advance. There is absolutely nothing like a night under the stars in one of their private gazebos. Farm to table, unforgettable.
🔸Nightcap: Luna Rooftop Bar
Back in Portland - head to this covered rooftop bar overlooking Portland’s working waterfront!
→ Additional late-night options: The Danforth, Paper Tiger, Room for Improvement
🔸Activity #1: Eastern Promenade Stroll
Kick off your last day strolling the Eastern Promenade. Begin your walk where Commercial St becomes Thames St. & wind past Fort Allen Park to the top of the hill for stunning views.
🔸Brunch: Crown Jewell (Great Diamond Island)
Hop on a Casco Bay Lines ferry to Great Diamond Island (30 min trip.) A perfect way to get out on the water, take in the sights and land at a beautiful island for great food + drinks.
Itinerary #2 (crappy weather)
🔸Pre-Dinner: Portland Museum of Art
Admission is free to the public every Friday from 4PM-8PM!
🔸Dinner: Wayside Tavern
Take a quick walk from the museum to find this gem. Snag a spot at the bar & devour the olives, the cod cheeks and tonnarelli.
🔸Breakfast: Belleville, Norimoto or Night Moves (South Portland)
You can’t go wrong with a pastry, treat or coffee from any of these spots.
🔸Activity #1: Terrarium
A garden center & hub for DIY terrarium creations - with a mini bar/cafe on site! Enjoy a coffee (or wine!), join a workshop, or create independently with help from the awesome staff!
🔸Lunch: LB Kitchen, Ramonas, or Radici
Grab a grain bowl & smoothie from LB Kitchen, a generously sized hoagie from Ramonas or addicting pizza from Radici.
🔸Activity #2: The Cellars at Allagash
Hidden behind Allagash Brewing Company find The Cellars. Enjoy a one-hour guided tasting and wild barrel room tour. Book in advance!
→ Want to skip drinking? Head to the Portland Flea-For-All on Congress Street. Only open Fridays & Saturdays - peruse incredible furniture, housewares, clothing and vinyl.
There is nothing like enjoying dinner on the working waterfront no matter the weather. Beautiful, spacious, elegant, delicious - with all of the seafood you can stomach!
→ Additional upscale options: Street & Co, Leeward, Chaval
🔸 Breakfast: Rose Foods
I mean, you can’t leave Portland without getting one of these bagels. You just can’t.
🔸Activity #1: Old Port Shopping
People always say to explore the Old Port when visiting - but to do what exactly? Well, here are some of my favorite shops to duck into: Loquat, Blanche & Mimi, Portland Dry Goods and if you feel parched after shopping, grab a beer at the hidden Novare Res or throw one back on the patio at The Thirsty Pig.
Itinerary #3 (bring the kiddos)
Disclaimer: I bring my kid pretty much everywhere with me - so, this isn’t to say you can’t enjoy the above itineraries with your kiddos. With that said, the below is fool proof, supremely kiddo-friendly, and actually fun for you too.
🔸 Pre-Dinner: Thompson’s Point
Learn about Bigfoot at the Cryptozoology Museum, let the kiddos play at the incredible Children's Museum & Theatre of Maine and grab a pint (for the adults) at Bissell Brothers.
🔸Dinner: Summer Sunsets at Thompson’s Point
Thursdays & Fridays throughout the summer hop over to Summer Sunsets to enjoy local food trucks (get everything from the Mr. Tuna & Crispy Gai trucks), live music, cocktails & a gorgeous sunset! Huge space for the kids to run around - plus the entry is free!
🔸 Breakfast: Scratch Bakery & Willard Beach (South Portland)
Grab the best sea salt bagel, dog treats & whatever pastry is calling to you - and then walk around the corner to Willard Beach to beach stroll. There’s a playground at the entrance!
🔸 Activity #1: Two Lights State Park (Cape Elizabeth)
A breathtaking, 1 mile loop along the water. Pocket beaches to explore, rocky cliffs to climb - I’ve gone oh so many of times and never tire of it.
🔸 Lunch: Bite Into Maine at Fort Williams (Cape Elizabeth)
Let’s get you that lobster roll! My favorite is from a food truck in Fort Williams. Visit Portland Head Light, let kids run free (children’s garden!) & eat lobster (or grilled cheese) by the sea.
🔸Activity #2: Bayside Bowl
Bowling is always fun - but once you finish a game, you must make your way to their rooftop! Enjoy great cocktails and expansive views of all of Portland!
→ Prefer an outdoor activity? Haul in lobster traps with Lucky Catch Cruises!
🔸 Dinner: Black Cow Burgers
I genuinely love the burgers here. Such an easy spot right in the Old Port - lots of space, plenty of tables and there is a mini game room where the kids can play while they wait for dinner!
→ Additional laid back options: Salvage BBQ (often live music, counter service, large), Lukes Lobster (right on the water, dedicated kids menu), Pai Men Miyake (get the brussel sprouts! Delicious ramen, kiddo friendly), Lazzari (great pizza, laid back vibes!), Lenora (tacos!)
🔸 Dessert: Portland Twirl
Get a treat for the kiddos (and you, duh) at this unique soft serve spot located on the first floor of the Public Market House. If they have it: get the Self Care Sundae….trust me.
🔸 Breakfast: Dutch’s
A counter-service fixture in Portland where kiddos are welcome. Everything is delicious - but be sure to get the hashbrowns.
🔸 Activity #1: Mackworth Island (Falmouth)
Just 15 minutes from downtown Portland, this sweet 1.25 mile island stroll is not only picturesque - there is so much for the kids to explore: fairy houses, beaches & more!
Please oh please add your favorites & must dos in the Portland area in the comments!