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Kristin Klarkowski works as an early childhood educator in Minneapolis with her husband Tony and her two sons Bennett and Teddy. She is an early riser, hobby knitter, and exceptional home cook who loves spending time outdoors. She is the sole planner for most of their family vacations and strives to strike a balance between adventure and relaxation.

Where are we going?

Northern Maine, from Portland to Bar Harbor.

We’ve always done a good job of exploring the US, taking advantage of every long weekend and school break visiting capitol cities like NYC and D.C. In our summers off we go for a bit more adventure in places like The Black Hills and Glacier National Park. However, our summer road trip to northern Maine was one of our very favorite family vacations. We divided our time between Portland, Waldoboro Village and Northeast Harbor. It was a wonderful combination of spontaneous adventure and leisurely exploration.

When should we go?

They say the best time to visit the east coast is between June and October.

We traveled in August, and while it was steamy in Portland it wasn’t too bad when we were out near the coast. Even in mid-summer, temperatures in coastal Maine can be cool, with daytime highs reaching only the mid-70s. If you wait until after Labor Day you can enjoy the charming seaside towns with even mild temperatures and less congestion. Or wait until October, when the temperature really dips and you have the opportunity to see the spectacular foliage. The good news is that no matter when you go, you can always get good lobster.

How do we get there?

We flew from Minneapolis direct into Portland. The airport is easy to navigate and we quickly picked up our rental car. We stayed in Portland the first night and started our drive early the next morning. We held up in Waldoboro for two nights, before moving to Northeast Harbor for the following two. Then back to Portland for our final two nights in the city. The views on Hwy 1 are incredible, and although we had an inn keeper tell us to fly into Bangor next time, I wouldn’t want to miss the drive along the coast. Maine’s Route 1 road trip is as quintessential New England as you get.

Where did you stay?

In Waldoboro Village,

We stayed at Pennysworth on Thistledown Farm, which is an re-purposed post and beam barn house on the end of a quiet dead-end road. There is a large stone terrace, indoor and outdoor fireplaces, a huge fire-pit with an endless supply of wood, and a fantastic loft for the boys. Their little peninsula has a wonderful freshwater swimming hole, saltwater boat launch, two preserves and beautiful vistas. But the best part of the property is that it was once home to The Maine Float Rope Co., and I had the opportunity to make a handmade basket and rug, woven from reclaimed lobster trap rope, with owner Penny, a former weaver for Down East Door Mats.

In North East Harbour,

We stayed in a private maritime-style Airbnb build by a local architect. It had all the provisions needed, including a grill, smoker and even a lobster cooker in the backyard. The neighborhood location offered us a glimpse at seaside living in quaint mid-coast Main

“Our hosts Marcia and Commodore Denny were extraordinarily hospitable. They took us out on their yacht and they even let the kids drive. It was a remarkable memory.”

In Portland,

You aren’t going to get a pool (if that’s important) unless you go with a chain hotel. That’s just the way it is. Instead go for The Francis, which is a historic landmark property situated in a neighborhood near the art district and one of the two Holy Donut locations. It has a spa and only 15 rooms. If you’d prefer a larger hotel and want to stay on the waterfront, The Portland Harbour Hotel is a nice choice and some of the rooms offer both a living space and a view. Alternatively, if you want to rent a house, then look for one in Portland’s West End, Scarborough Village.

Rtip: If you are looking to extend your stay or add a stop along the way, you should consider Chebeague Island Inn, recommended by Roam Guide contributor, honored wedding photographer and friend Liz Banfield. Alternatively we’d recommend a stay in The Squire Tarbox Inn, a country inn with onside wood fired pizza and only 12 rooms.

Photo Credit : Liz Banfield

What should we do?

In Portland,

The peninsula is just three miles long, so you can easily walk from end to end. Just get out exploring and you’re sure to discover a local favorite.

I highly recommend doing the Mail Boat Run. It’s really easy to get tickets in the morning and I suggest you go on the earliest boat. You literally hop on board and spend the day delivering the mail to islanders on five coastal islands. The entire working waterfront is home to lobster-men hauling traps, cargo ships and harbor seals. The round trip will take you the day so you’ll want to pack a cooler with lunch and plenty of sunscreen. If you aren’t up for all the stops you can opt for Peaks Island, were you can rent bicycles and explore (it’s four miles all the way around). There are some great beaches closer to town that are perfect for a picnic. Just don’t miss the “back boat” or you’ll get stuck. There is only one way on and off the islands until the next day, and that’s the mail boat.

If you don’t have time to fit in the Mail Boat Run, you really should consider getting out on the water later in your trip. I’ve heard good things from two sources about the little ferry ride to Vinalhaven from Rockport. Also the schooners that sail out of Camden, particularly the two-hour day sail offered through, Schooner Surprise.

Rtip: You can't legally go lobstering unless you're licensed to do so, and acquiring fishing license isn't easy. In fact, you can't get one at all if you aren't a state resident. However if you’d like a glimpse at lobstering you can book an excursion with Lucky Catch, which is more of a tour guide who shows and teaches you about trapping. You can’t keep any of them unfortunately, but the owner is a commercial lobsterman, very personable and informative.

On our way out of Portland we stopped at the Maine Maritime Museum. Maine has quite a maritime history, and you don’t have to be into watercraft to enjoy the exhibits or appreciate the magnificent on site schooner.

Rtip: The museum diversion is near the Boothbay hiking region, as well as Reid State Park’s mile long sandy swimming beach, and the aforementioned Squire Tarbox Inn. If there is time in your itinerary, Ovens Mouth comes highly recommended for its scenic coves, salt marshes, and stunning nature trails. This area could easily be added to extend your itinerary.

In Waldoboro,

We took several day trips. Our favorite was Cliff Diving at Peters Pond in Waldoboro’s Quarry Hill. A recommendation from our Airbnb host, it was a spectacular experience, especially for our boys. No crowds- just a glorious quarry pool with stunning 360 views of the preserves and a lot of laughter.

We also really enjoyed the Pemaquid Point Lighthouse & Beach. We stopped for sandwiches and sodas at Waltz Soda Fountain on our way. We ordered homemade Lime Rickey’s that were incredible. Lucky for us, the beach had sand toys for rent. Generally, my kids are not beach kids but they really enjoyed this one- I think the sand toys helped. After the beach, we climbed a steep rocky cliff to tour the lighthouse.

A third day trip to consider is the Port Clyde Peninsula. There are several beaches to explore as well as the Marshall Point Lighthouse, which sits at the mouth of the St. George River in the picturesque fishing village of Port Clyde. The authentic white lighthouse from 1858, houses a keepers' quarters as well as a summer-only museum and gift shop. Several evenings a week you can also take a two-hour Puffin and nature cruise out of the harbor which is wonderful.

On our way north from Waldoboro we made an interesting stop at the Maine State Prison Showroom, where they sell novelty items and crafts made by the prisoners. They also have giant cutouts of prisoners where you can pop your head through and get a photograph- who knew?

Marshall Point Lighthouse Travel Guide.jpg

In Northeast Harbor,

Picture a town full of upper crust New Yorkers, all with gorgeous little summer cottages, cruising around on ramshackle bikes with all the time in the world. There are only seventeen streets in Northeast Harbor so I really enjoyed walking the quiet neighborhoods in the morning, gazing at all the charming properties and people watching.

“What an idyllic place to spend your summers, filled with bike rides, BBQs, and Seafood boils.”

Don’t miss a trip to Thuya Garden Preserve. We hiked up to a point where you can overlook the entire harbor, and it is stunning. It doesn’t take long so it’s an easy thing to slide into early morning or late afternoon. If you can, I’d also suggest taking a boat out in the harbor one foggy morning.

Be sure to spend a day exploring Acadia National Park, it is just breathtaking. You can start with a drive along Park Loop Road which gives you a good sense of the entire park. You can literally see everything. The road leads through granite rock formations to “Sand Beach” which is actually made up of finely ground shells and the spines of sea urchins. The water is icy but the sea view is expansive. I’d also tell you that carving out time to hike Cadillac Mountain Summit, and getting afternoon tea and popovers lakeside at Jordan Pond restaurant, are both worth the effort. Acadia is known for its carriage trails which is another great way to see the park, especially with little kids. If you’re interested, you can rent bikes through Acadia Bike.

Rtip: While a lot of folks head to Cadillac Mountain for the sunrise, there are plenty of good places from within the park to see the gloaming. The first is the shore along Ocean Drive and the other is the smaller Gorham Mountain. For more ideas as to what to do in Acadia, see our Roam Guide from park enthusiasts, The Park Chasers here.

Travel Guide to Bar Harbor Liz Banfield.jpg

Photo Credit: Liz Banfield

Where should we eat when we’re there?

Maine is rife with local lobster shacks offering fresh off the boat seafood and plenty of local charm. In August it’s the homemade blueberry pie you’ll want to seek out.

In Portland,

We went to Lobster Shack Restaurant on the water at Two Lights where they still make everything by hand. It’s literally a shack in the middle of nowhere. The area is known for the glorious Cape Elizabeth lighthouse and its choppy shoreline so if you can make time to climb along the rocks, you should.

One night we enjoyed a pizza at Espo’s Trattoria, a neighborhood joint recommended by a friend. Unfortunately like so many long standing restaurants, it has since closed its doors due to Covid-19. A new owner took over the building and renamed it Maria’s but we have no first hand intel on the food. If you’re craving pizza, you could try traditional Italian bakery Micucci instead, where you can get giant billowy slabs of exceptional pizza as well as pick up some authentic Sicilian sauce and oil.

Rtip: If you’re always on the hunt for oysters, like us, check out the Eventide Oyster Company, which also has it’s own version of a lobster roll, served on Chinese steamy bun.

Along Mid-Coast Maine,

It’s likely you’ll need a place to stop for a bite along the road trip from Portland to Bar Harbor. First I’d suggest Five Islands Lobster Co., where Lobsters are pulled straight from the surrounding waters and are never “tanked-stored.” There is also McLoon’s Lobster Shack, a little further north near St. George. It’s an institution when it comes to Maine lobster. Also look for the tiny Cafe Miranda or the more upscale Primo farm to table restaurant in Rockland.

“While visiting Maine it is important that you get your fill of old-school chowder and lobster rolls, that is what the northeast is known for after all.”

In Waldoboro,

We enjoyed breakfast with our airbnb host and packed day trip picnic lunches. One night we drove to the nearby town of Round Pond to try the popular village restaurant, The Anchor and eat seafood. While we were in town we stopped at an adorable Candy shop, called Granite Hall Store where we had ice cream and browsed all kinds of chachkeys.

Rtip: There is quite a diner culture in Maine and Moody’s Diner is great for a sit down lunch. It’s an un-fancy spot that’s has been in business over 80 years and the perfect place to sample a seasonal fruit pie.

In North East Harbour,

We did a lot of grilling at our rental and after a long day exploring that worked best for us. If that’s your plan I recommend you hit a grocery store in Bar Harbour for food because you’ll pay $10 for a head of lettuce if you shop in NE Harbor. The town of Bar Harbor itself is a bit touristy but you’ll save a lot of money if your plan is to “eat at home.”

Rtip: If you want to actually eat out, McKay’s Public House, is a good choice for locally caught seafood with a large outdoor patio space in Bar Harbor. Colonel’s Restaurant and Bakery is our choice in NE Harbor, with it’s daily pastries and long list of specialty sandwiches.

Where can we grab a cold beer?

Just outside of Portland on your way north you’ll find the Maine Beer Company, craft brewery and tasting room. They have a nice outdoor patio and wood-fired pizzas. In Portland, check out Austin Street Brewery.

Tell us something we don't know?

Lobsters are caught in traps that are strung together and attached to buoys on the surface of the ocean. When floating lines are used to connect the traps they form a spider web of ropes that can entangle North Atlantic right whales. 10 years ago they switched from synthetic rubber “float rope,” to natural “sinking” trap rope for conservation purposes. You’ll see now that its big business to use reclaimed lobster trap rope to create everything from baskets to doormats. Because each fisherman had their own color identification the design combinations are endless.

Where can we shop?

I personally loved More & Company outside of Portland in Yarmouth on Hwy 1. It’s a designer goods shop and cafe. I’ve also heard the The Angela Adams studio showroom in Portland is awesome for design nerds. She makes rugs, textiles and furniture inspired by the landscape of Maine (she grew up on an island).

In Northport (near Camden), the Swans Island Blanket Company is definitely worth a visit. The blankets are woven onsite in a post and beam farmhouse and the blankets are heirloom quality.

“These blankets are beautiful and we actually have one at the end of our bed just in case we need a little cat-nap during the day.”

What should we take with us on the trip?

Microfiber or quick-dry packable towels, multiple swimsuits, a soft cooler, and a Swell or hydro flask water bottle for each person in the family. I always have a daypack; my pick is Fjallraven but my husband loves NorthFace. I bring lots of sundresses and my Apple watch, and I’m good for days. I’d suggest a pair of solid walking shores, not hiking like you are going to the boundary waters, but something sturdy and comfortable, as well as a pair of slide-on sandals.

What’s the one can’t miss item on your itinerary?

For sure it was cliff jumping at Peter’s Pond. We were the only ones in sight and it was a highlight for sure.

What will you do differently on your next trip?

I looked seriously at staying near Camden at the Lincolnville Motel. Next time I might check out some of the day hikes in Camden Hills State Park, most of which take less than two hours and offer fantastic views of the bay (so I’m told). There is also a cooking school called Salt Water Farm that peeked my interest. Classes vary from traditional country cooking to how to bake a pie, plus everything you’d want to know about home seafood prep.