Blueberries, Breads & Boutiques: Your Travel Guide to Portland, Maine

July 10, 2023

lighthouse in Portland Maine

Nestled right in the middle of this coast-heavy state, Portland, Maine is the most populous region of Maine, offering the traditional coastal charm with a twist.

Unlike the bougie Cape Cod and the Hamptons, Portland, Maine deviates from the ‘coastal charm’ city with its vibrant, quirky food scene and its emphasis on the arts, making it the perfect destination for those looking for an upscale hipster experience without the high-class budget. 

If you’re ready to plan the ultimate Portland, Maine trip, read on below.

Portland, Maine Travel Tips

Where We Stayed

Portland, Maine is filled with historic accommodations, from 19th-century bed-and-breakfast spots like the Chadwick to waterfront stays at Canopy by Hilton.

For our trip, we chose a historic AirBnB that was previously owned by a confectioner named Benjamin Rolfe Jr. This 1848 Greek Revival boasted two elegantly laid out bedrooms, a cozy reading room with games, and an updated kitchen and bathroom for modern-day amenities. With all the interesting books and architecture, we could have spent our whole time in Portland exploring this AirBnB alone!

Can’t-Miss Restaurants & Bars

margarita at Taco Escobar

There’s a reason Bon Appetit named Portland, Maine “America’s Foodiest Small Town.” In a few short hours you’ll discover the many restaurants that Portland has to offer. During your visit, make sure to check out at least one of the following destinations:

Taco Escobarr

If you’re a taco-lover like me living in Boston, you know good Mexican food is hard to come by in the Northeast. That’s where Taco Escobarr comes into play. Offering freshly made chips and salsa, along with a variety of fun and flavorful tacos, we wound up eating here twice because it was so good. My advice? Don’t skip out on the margs with your dinner. They’re 100% worth it.

Menu Here: 

Green Elephant

Perhaps some of the best Thai food I’ve had in my life, Green Elephant is completely vegetarian and the perfect healthy meal to recover from a day filled with fried donuts and tacos. Offering everything from mouthwatering Pad Thai to Tofu Tikka Masala, you can’t go wrong with anything on Green Elephant’s menu.

Explore here:


It’s truly not a Portland, Maine trip without a visit to Portland’s secret speakeasy where, if you can get in, every drink costs a Lincoln ($5). The inside is delightfully charming, with dim lighting and a cozy bar feel. Make sure to bring cash, though, since Lincolns is cash-only and does not take card or Apple Pay. You’ll find Lincolns at 36 Market Street. But how to get inside? I’ll never tell. 

Boutiques, Books & Bakeries

woman walking out of a store with a price flag

Once you’ve had your fill of Portland, Maine’s delicious food scene, you’ll next want to stop into the gorgeous shops of downtown Portland. For books, you can’t miss Longfellows or Print, which both offer an eclectic range of books and souvenirs. 

Our favorite boutiques included Blanche & Mimi (offering new and vintage treasures), Pinecone + Chickadee for oddities and Maine-inspired gifts, and Portland Trading Co. for high-end fashion. For the avid thrifter, don’t miss out on all the Portland thrift action from Portland Flea for All and Little Ghost Vintage to Material Objects for stylish thrifted clothing.

After all your shopping, be sure to stop by at the Portland, Maine staple, Holy Donuts which may very well be one of the top-two donuts I’ve had in my entire life. Made by potatoes (yes, really—potatoes) these donuts come in a variety of flavors from pomegranate and lemon to toasted coconut and vanilla sprinkle. Don’t let the potato fool you, these donuts taste fluffier and lighter than any Dunkin you’ve ever had. And the best part? These donuts are 100% vegan thanks to their potato batter. 

Best Blueberry Spots

Holy Donut blueberry donut

You can’t leave Maine without trying their famous Maine blueberries. Luckily, Portland, Maine is nothing short of a blueberry-lover’s paradise. When in Portland, try out these blueberry-flavored items:

  • Two Fat Cats Bakery: Wild Maine Blueberry pie
  • Holy Donut: Maine Blueberry Donut
  • Standard Baking Co.: Blueberry Oatmeal Scone
  • Allagash Brewing Company: Wheat Ale with Fresh Maine Wild Blueberries (seasonal)

Lighthouse Hop Along the Coast of Maine

lighthouse in Portland Maine

Once you’ve finished shopping and dining to your heart’s content, Portland, Maine has a wide variety of activities to keep you entertained throughout your entire stay.

During my visit, we spent one day lighthouse hopping and exploring three of the five local lighthouses in the Portland region. Starting our tour at Portland Head Light, we began with a brunch picnic along the grassy top before exploring the lighthouse and nearby abandoned building. Portland Head Light is one of the most photographed lighthouses in all of America, and the dramatic background you see when you arrive indicates why. For those interested, you can go inside and see the museum, or skip to the next lighthouse: Spring Point Ledge Lighthouse.

Spring Point Ledge was my favorite lighthouse of the trip, mostly due to the rock hopping needed to get to the bottom of the lighthouse. Make sure you wear sturdy shoes, as some of the cracks between the rocks are wide and far apart.

After exploring Spring Point Ledge, we finished our day at Bug Light, the most elegant of the three. For all the lighthouses, there is free parking available in the nearby region. 


With picturesque lighthouses and freshly picked blueberries, there’s nothing quite like Maine in the summer. Add Portland, Maine to your summer bucket list to enjoy this surprisingly crunchy coastal town in all its beachy charm. 

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Photo: Dana Drosdick

Dana Drosdick
Dana is a marketer living in Saratoga Springs, NY with a passion for all things related to stewardship, faith, wellness, and personal enrichment. Her work has been featured in various Chicken Soup for the Soul anthologies, The Odyssey Online, and The Banner Magazine. Follow her at @danadrosdick on Instagram for foodie trends, her latest book recommendations, and far too many photos of clementines.


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