Where to Eat in Portland, Kennebunkport & Kennebunk in Maine

It should be freezing cold and everything should be buried in snow. Instead the cobblestone streets of Old Port are wet with melting slush and snow, though most of the shops in the area are closed when we arrive in the area around 5 p.m. as if we should all be retreating to the hygge of our homes to hunker down against the elements.

Despite the “sleepy town” feel everywhere we went, my teammate Jared and I used our little bit of spare time on a recent business trip to explore the area and uncovered a few gems worth sharing. Warning: It’s nearly all food.

The first thing I did after parking my car in the Old Port area was snap this sunset photo over the Fore River that connects to Casco Bay – then hit up the nearby valet for some recommendations.

Sunset Over Fore River Waterfront in Portland, Maine
Sunset over the Fore River that connects to Casco Bay

Independent Ice Company

Independent Ice Company was a quiet little whiskey bar in the Old Port area with leather booths, wood grain, candlelight, and a red backlit bar. Though it was almost empty on a Monday evening, the spot had a pleasant ambience and provided respite from the cold. The server had control of the playlist, and had Charles Bradley on rotation. I enjoyed the Kolsch from local Maine brewer Orono.

Orono Brewing Kolsch at Independent Ice Compan
Kolsch beer from Maine local brewer Orono at Independent Ice Company


Our visit to Scales was our “splurge” meal of the Portland business trip. Jared looked up the best restaurants in the area for oysters. Right away we ordered a dozen east coast oysters and a glass of wine each. It’s always fun tasting half shell varieties with friends, and we enjoyed their local Basket Island, New Meadow and Wolfe’s Neck oysters.

We also ordered the wholly unnecessary (and wholly worth it) cloverleaf rolls with garlic butter. There was a strong debate between the lobster roll and their whole lobster special, but we ultimately both went with the special.

Brought to our table was a massive whole lobster split down the middle and buried in a butter wine sauce, a particularly herbaceous-tasting tail, and extra tender claw meat.

Scales Restaurant Door in Portland, Maine
Oyster Bar at Scales Restaurant in Portland, Maine
Fresh Catch of the Day at Scales Restaurant in Portland, Maine

Glorious Gelato

We satisfied our after-dinner sweet tooth at Glorious Gelato, a true Italian gelateria founded by a Milanese couple 10 years ago. I treated myself to the chocolate hazelnut gelato on a waffle cone. Delicious.

Hazelnut Gelato at Glorious Gelato in Portland, Maine
Hazelnut gelato at Glorious Gelato

With all the purple interior decor with pops of yellow it was like the anti-Planet Fitness. I regret nothing. We made sure to check with our gelato server on the way out the door for a breakfast recommendation. Which leads us to…


Breakfast at Dutch’s! What an awesome recommendation. The moment you walk in the door you are surrounded by quaint, old-fashioned posters advertising the outdoor attractions Maine has to offer. The diner vibe is strong in this hipster-friendly haven.

Dutch's Diner in Portland, Maine
Dutch’s is right out of a postcard

I wanted to eat 80% of the menu, but I ordered the extremely tasty vegetarian breakfast burrito which came filled with scrambled egg, cheddar, hash browns, refried beans, salsa, chimichurri, and sour cream wrapped in a flour tortilla.

Vegetarian Breakfast Burrito in Portland, Maine
Vegetarian breakfast burrito

One Six Green

When you are going into all-day client meetings to do great work together, you need a little caffeine to keep your energy and attention up. So we popped into One Six Green, a small shop owned by Australian expat Kharis Johnston.

Coconut Milk Latte & Americano at One Six Green in Portland, Maine
Coconut milk latte at One Six Green

Pro-tip: I brought my own reusable mug, but Kharis was quick to offer one of their “give a mug, take a mugs” for Jared’s use.

Spring Point Marina

We had some time to kill before we had to hit the road to Kennebunk, the weather was nice, and we wanted to see a lighthouse. The nearest one was Spring Point Ledge Lighthouse. This is a real, functional lighthouse that has been here since 1897.

Spring Point Ledge Lighthouse & Stone Breakwater in Portland, Maine

I’m not going to lie, we laughed when we saw how squat it was. But it turns out this is a caisson-style light station, and it’s the only one in the U.S. you can actually walk to!

The lighthouse closed to interior visits – it’s open only Memorial Day through Labor Day. It was still such a nice stop on an unseasonably beautiful winter morning. I wish I had been wearing more casual shoes to be able to make my way down the stone breakwater.

Victorian House near Kennebunk

Speaking of the commute to Kennebunk and Kennebunkport from Portland – check out this wild yellow Victorian house we spotted on the side of the road! There were so many big, ornate homes like this on our drive.

Yellow Victorian Home Near Kennebunk, Maine


When we arrived in Kennebunk, we wandered around the blink-and-you’ll-miss-it town for a bit prior to our meetings. We popped into this lovely little bakery, Boulangerie, for a pastry.

Fresh Artisanal Bread at Boulangerie Proper Bakery in Kennebunk, Maine

It looks like a big, red barn with lots of rustic wood textures inside. Such a cozy place to hole up with a friend and some pastry.

Boulangerie Bakery in Kennebunk, Maine
Boulangerie, a “proper bakery” in Kennebunk

This “proper bakery” serves artisanal bread ranging from baguettes to loaves to danishes to quiche. You can also pick up a light lunch, coffee or tea, and a few local wares. I opted for the perfectly flaky, buttery croissant.

Fresh Croissant from Boulangerie in Kennebunk, Maine
Is there anything better than a perfect, fresh croissant?

The Boathouse Waterfront Hotel

Our client recommended the Boathouse Waterfront Hotel for dinner, and it was a great time! The bartender who had migrated across the country from the other Portland was great company during cocktail hour while we awaited the rest of our party.

Waterfront View at Boathouse Waterfront Hotel & Restaurant
Sunset on the Kennebunk River

She allowed me a little time to check out their beautiful waterfront patio and snap a few photos.

Fire Pit & Lighting at Boathouse Waterfront Hotel & Restaurant

I ate everything at the Boathouse. As appetizers for our large group, we circulated two dozen chef-selected oysters (of which I had more than my fair share), the Maine Crab Cakes with pickled slaw and Green Goddess dressing, the lobster fried rice with sesame egg and Napa cabbage, and ridiculously good crispy Brussels sprouts with Sriracha, honey and lime.

New England Home on the Kennebunk River

To top that off, I also ordered the lobster roll for my main. It was served New England classic on a New England roll with mayo, lemon and chive. I practically had to be rolled out of there.

Sunset on the Kennebunk River at Boathouse Waterfront Hotel & Restaurant
Sunset on the Kennebunk River

This meal was enough to make anyone fall in love with Kennebunkport.

#lovekpt Love Kennebunkport
Love Kennebunkport

The Holy Donut

In case we hadn’t eaten enough the night before, we sought out the famed “potato donut” from The Holy Donut at their original location on Park Ave. How much do you love this colorful display of deliciousness?!

The Holy Donut on Park Ave. in Portland, Maine
The original Holy Donut location

And what is a potato donut you ask? According to their website, “The (not-so) secret ingredient: fresh Maine potatoes. Adding mashed potatoes gives the donuts a delicious moist texture that makes them just melt in your mouth.”

Potato Donuts from The Holy Donut in Portland, Maine
Dark chocolate sea salt and ginger-sugared sweet potato donuts

I can attest. I had their dark chocolate sea salt donut (right up my alley, and apparently their most popular flavor) and enjoyed it, but the real winner for me was their ginger-sugared sweet potato donut, made with roasted sweet potato and Maine potatoes in the dough.

Despite their massive growth since they opened in 2012, the shop still hand-cuts every donut, and aims to source as many whole ingredients locally as possible. Should they ever have a day when they don’t sell out, they donate all leftover donuts to a local food pantry.

Isa Bistro

On our way out of town, we elected to have a little healthier meal after all our indulgences of the day before. We needed a meal at an odd time, and were lucky to find Isa Bistro open around 2 p.m. for lunch.

This spot was cozy yet felt upscale with its brick, dark wood, black-and-white tile, and beautiful warm lighting.

Isa Bistro Interior in Portland, Maine
Interior at Isa bistro

For a starter, we split the shaved fennel salad, with grapefruit slices, thin wedges of pecorino cheese, mint, a delicate vinaigrette and fresh-cracked pepper.

Shaved Fennel Salad at Isa Bistro in Portland, Maine

Jared had the meaty beef osso busco stew with hearty carrots, potatoes and grilled bread.

Beef Osso Busco Stew at Isa Bistro in Portland, Maine

I ordered their lobster tacos on soft corn tortillas with fennel, thinly-sliced radish, zesty guajillo aioli, and a garnish of fresh cilantro. On the side was a lightly dressed greens salad.

Lobster Tacos at Isa Bistro in Portland, Maine

I couldn’t ask for a brighter, fresher close to an unseasonably warm trip to Portland, Maine and nearby Kennebunk and Kennebunkport. I’m eager to get back soon!

8 thoughts on “Where to Eat in Portland, Kennebunkport & Kennebunk in Maine

  1. Ellen Evins says:

    That Victorian house youphotographed is known as the Wedding Cake House. It was built by a groom for his new bride! I have been summering in Kennebunkport since I was a child and have many fond memories of driving by it.

    1. Heather says:

      Wow! What a perfect little name for that house! It really caught my eye on the drive. ๐Ÿ™‚

      1. Matt says:

        I drive past the Wedding Cake house a couple times a day because I live in Kennebunk. Next time you drive past, take a closer look. The house is actually rotting and falling apart from lack of upkeep. No one lives there, and the family of the previous owner do not want to spend the tremendous amount of money to restore the ornate facade. It’s an issue for the town

    2. Diana Erickson says:

      We stayed at Captain Lord Mansion during our fall leaf peeping trip last October. Loved the charming trolley tour and the local lobster rolls. Such a charming community.

  2. Ginger says:

    I stayed in Kennebunkport for a long weekend . I walked to Boulangerie every morning for coffee and treats. I must have put on 10lbs in those 3 days! But oh so worth it.

    1. Matt says:

      If you stayed in Kennebunkport, you probably weren’t walking to Boulangerie. That would be about a 8 mile round trip. Boulangerie is in downtown Kennebunk. Two different towns

      1. Heather says:

        Thanks for your -several- comments, Matt. I appreciate you reading. To clarify, I’m aware they’re two towns – we stayed in one of the two towns, and our client’s office was in the other of the two towns, so we spent time in both. I wish I had more time, and hope to visit again soon, but it was a short business trip.

  3. Matt says:

    No offense, but for an article entitled “Where to eat in Portland, Kennebunk, and Kennebunkport” you only reviewed 1 bakery and no restaurants in Kennebunk, and 1 restaurant in KPort. There’s many more choices in KPort for certain, and some great local spots. Your title was misleading

Comments are closed.