Portland, Maine

Coolstuff Team
March 1, 2024

Portland, Maine is a place we’ve been to kind of a lot. Over the last 5 years we’ve been nearly 6 times and have come to make it an annual trip to soak in the views, become inspired, and eat really, really great food. There are a lot of places spread out across the Portland metro area so we definitely advise driving from the city or renting a car upon arrival. Here are some of our favorite places to enjoy the best of coastal Maine! 


The Francis Hotel

Whenever we visit a new city, we’re always looking for a place to stay that has character, great staff, and is in a walkable neighborhood. We love The Francis because it has all three! Right on the intersection of Downtown, Parkside, and the West End, there are so many great spots nearby – including the Wayside Tavern downstairs and Tandem Coffee & Bakery across the street. 


Wayside Tavern

The Wayside Tavern, right downstairs from the Francis Hotel, is one of our favorite spots to eat in Portland. From the cozy main dining room to one of the two historic rooms from the Francis hotel, the vibes are immaculate. We love their take on new American food with an nod towards local ingredients, and appreciate that they aren’t afraid to have fun from time to time. Case and point: every Sunday and Monday are “burger night” and reader, this burger is awesome.  

Bread & Friends

This newcomer to the Portland dining scene got its start slinging bread at the farmers market and has expanded into an airy and modern dining room serving the best breakfast on the East Coast (we mean it!) From the crispiest breakfast potatoes to soft scrambled eggs with a caramelized onion jam, Bread & Friends is making classic brekkie new again. 

Special thanks to Ana Inciardi & Addy Wagner for showing us this gem! 

Crispy Gai

If you’re looking for a fun time and great food, don’t miss Crispy Gai. This spot serves fresh and fun takes on Thai food like their Hat Yai chicken and Pad Pok Brussels Sprouts.

Rose Foods

A much loved deli that benefits from its fantastic branding by the Atlanta-based firm Family Bros. Our favorite thing is the rye bagel - a little twist makes for a nice change of pace! 

Red’s Dairy Freeze

Open during the Summer season, Red’s Dairy Freeze is a South Portland institution. Selling surprisingly affordable soft serve and other frozen classics, Red’s is the best place to stop for a sweet treat on the way to or from one of Portland’s many lighthouses. 

Tandem Coffee & Bakery

This little spot inside of an old auto body shop turns the volume up to ten. They roast amazing coffee just across town and crank out a huge assortment of pastries every day. Our favorite treat to go along with a nice cup of mud is their daily breakfast sandwich which consists of eggs, cheese, and homemade sausage all atop a perfectly flaky biscuit with just the right hint of sweetness.

Izakaya Minato

Sure there’s a line but, unlike pancake spots in the West Village, the queue is justified at Minato. This Japanese spot casually serves inventive and delicious bites and even offers a nightly omakase experience if you want a taste of everything. Don’t miss out on their cocktails which are unsurprisingly also top-notch. 

Zu Bakery

While we sadly approached Zu moments before they sold out for the weekend, this new, James Beard Nominated bakery is at the top of our list. Stop by for everything from croissants to rye!

Eventide Oyster Co

It wouldn’t be Maine without a lobster roll, and our favorite is from Eventide. This buttery baby is small but mighty and goes down especially well after a few rounds of fresh oysters and some cold Maine beers.


One of the newer players in the Portland dining scene, Regards is a small plates restaurant inspired by connecting the cultures of Los Angeles and Maine. You can expect a well appointed dining room and a chic crowd sipping glasses of chilled natty wine.

Taco Escobarr 

On every trip there comes a time where you realize it can’t all be champagne and caviar. When that moment strikes in Portland Maine, we recommend pulling up a seat at the bar here and splitting an order of the steak fajitas. We promise you won’t be disappointed.



Coffee by day, cocktails by night (and day) along with small plates, a great retail selection and fun design make Smalls one of our favorite spots in Portland. We often plan to visit once and end up returning 3 or 4 times.

Ruski’s Tavern

Portland’s oldest bar, Ruski’s is a place where locals go to drink. We first stumbled in while waiting way too long for a table at a restaurant that used to be down the street and decided to stay a while and have our night at Ruski’s. No regrets here as the kitchen performs almost as strong as their drinks! 

Portland Hunt & Alpine Club

For a chill spot to grab a craft cocktail near the old port, check out Portland Hunt & Alpine Club. We love the bartender’s choice option on the menu too, so long as you’re will to leave your drink’s fate in the hands of a certified professional.

Maps Bar 

Beer is big in Portland thanks to its recent history of great craft breweries, and Maps is one of the best places to drink it. The cozy basement bar serves a wide, wide array of brews (as well as grilled cheese) and always has a great record on the turntable. 

Maine and Loire

Portland’s first natural wine shop still has among the best selection in town. We always stop in for a bottle of something we haven’t seen before. Even better, Maine & Loire has recently started serving wine during the day on Saturdays so you can pop in, try a glass of something you love, then buy a bottle to take with you!

Allagash Brewery

One of Portland’s first craft breweries, Allagash is also perhaps the best known. The brewery has classic beer hall vibes which in 2024 means that there will be bearded men who have babies in a $3k stroller. 

Maine Beer Co.

Pizza and Beer is a classic pairing and if you’re looking for a bite and a brew near the L.L. Bean flagship in Freeport, this is a don’t miss stop. We love Maine Beer Co’s commitment to sustainability as well!


Blanche & Mimi

One of our favorite shops (in the world!) is this small treasure-filled shop. Expect a mix of antique silverware, niche hand lotions, and every size of Weck jar you can imagine.

Viand Mercantile

A new shop to Portland, Viand is giving the people what they want: a perfect curation of art, jewelry and home goods. This shop is filled with eye-candy and inspiration abound.

The Post Supply

We love The Post Supply for their fun selection of handmade ceramics, select French clothing, and one-of-a-kind homewares.

Portland Open House

If you’re on the hunt for that perfect mid-century dining table, a wonderfully antique glass bowl or your new favorite vintage jacket, this is the place. This large light-filled space is packed full of thrifted goods and sourced antiques. 


Portland Dry Goods

This is the spot to grab all of the right gear to dress like a true Mainer. A trip isn’t complete without trying on a Barbour jacket and the coolest new classic tee at Portland Dry Goods. 


This small boutique serves up perfect kitchen accessories and more like food shaped candles, art prints, and hand-made tea towels. You’ll want one of everything. 


Portland Trading Co

This Portland classic is the place to go for the coolest new clothing and accessories. The curation is always different and we love discovering new imported products here.


This resident Japanese cookware store will wow you with the selection of knives and kitchen essentials. All designed with intention, each glass, spoon etc is looked at like art at Strata. 



We love stopping by this fermentation shop and cafe during our shopping tour. Grab a coffee, a congee to-go or a baked good from the counter.

L.L. Bean

If you have to ask…


Portland Museum of Art

We’ve said it time and time again, but this museum is one of our favorites. We’re always stunned at the shows this  museum puts on and the pieces that they have in their collection. Stop by the museum during your trip for a dose of inspiration. 

Maine College of Art & Design Galleries

These small college galleries are always rotating and always wow us. Check out what’s on view and head over after a bit of shopping. 

Portland Bug Light

Maine isn’t Maine without some lighthouses. Bug Light is alwaysalwaysalways our first stop when we get into town and we hope you love it as much as we do. 

Portland Head Light

For a bit of a drive into South Portland, Portland Head Light isn’t to be missed. This is the picture-perfect lighthouse complete with roaring seas and a great view. 

Eastern Promenade

We love taking a drive to Eastern Promenade, brekkie and coffee in tow from Tandem, and enjoying our start to the day with an absolutely peaceful view of the water. Recommended rain or shine!


Antiquing along US 1 

If you didn’t already know, Maine is a GREAT spot for antiquing. Just outside of Portland, drive along US 1 for antique store after antique store. Follow this map to catch them all. 

Palace Diner

Biddeford, ME

A trip to Portland isn’t complete in our book without lunch on the way to or from the city in Biddeford at Palace Diner. A small spot RENOWNED for its diner classics like the tuna sammie and pancakes, you can’t miss it! Cash only!