With its unspoiled nature, thriving culinary scene and friendly locals, Maine is a fantastic state to visit whenever you are in need of some vacation therapy. When I discovered Maine, I immediately fell in love with the slow pace of life here. I could even imagine myself retiring in one of the small quiet towns on the edge of a peninsula. Thanks to our amazing hosts who took us around, we really got to experience true Maine beyond the popular tourist destinations. In this post, I share with you a 7 days coastal Maine road trip itinerary that goes off the beaten path. Get ready for some scenic drives!
My experience in Maine was sponsored by MidCoast Maine & Island and DownEast Acadia. All opinions expressed are my own. This article may contain affiliate links, which means, at no extra cost to you, I may earn a commission if you make a purchase. Thanks for supporting!
When is the best time to visit Maine
The peak season for tourism in Maine is the summer from July through August. However, the nicest time is arguably September to October, when there is cool crisp air and the leaves turn into pretty shades of red, orange, and yellow. Maine has long harsh winters between November to April, a time that is generally not popular for tourists. Although, if you enjoy cold weather sports like skiing, winter in Maine can actually be paradise. However, it is important to keep in mind that many businesses may not be open if you visit during this time, so extra research about lodging and dining is recommended. Springtime from May to June is the shoulder season before things get busy, making it a great time to beat the crowd. Our Maine road trip itinerary is designed to be taken from Spring to Autumn.
Looking for more awesome road trips? Check out this road trip planner for east coast USA.
How to get to Maine
The Portland International Jetport Airport, located 3 km west of down town Portland, is a convenient way to get to Maine. A flight from New York City takes only a bit over an hour. PWM is the third most affordable airport in New England since it is serviced by several low cost airlines such as Southwest and Jetblue. Find a cheap flight to Portland Maine here.
Where to rent a car in Maine
Renting a car is essential as driving is the best way to get around Maine. There are many car rentals at the Portland Jetport Airport for pick up on site, including Enterprise, Alamo, Avis, Budget, National, and Hertz.
Maine Road Trip Itinerary Day 1 & 2 – Portland
Start your trip in the biggest city in Maine, Portland. Portland’s name comes from the old English word Portlanda, which means “land surrounded by a harbor”. This waterfront city has many charming neighborhoods and lots of things to do. Spend the first two nights here to sightsee and gather yourself for the big road trip ahead.
Things to do in Portland Maine
Since there are so many options in Portland, I will offer some of my favorites. Feel free to mix and match activities that suit your interests.
Visit Portland Head Light House
This iconic lighthouse has been the subject in many postcards and paintings. Perched on a hill with waves crashing on to the rocks below, the Portland Head Light is a striking vision. Out of the 65 lighthouses in Maine, this is the oldest one. Visit in the morning and enjoy the scene in serene solitude.
Walk around the Old Port
Walk down the cobblestone streets of the Old Port District and get to know Portland’s history. You can see a mix of the old and new with 19th-century brick buildings and fishing piers being close by to modern shops, restaurants, and bars. This is the area where you will find the best nightlife.
Do a Foodie Tour
Portland is heaven for foodies. Besides the signature lobster roll, there are so many other good eats. What better way to try them all than going with a local expert? We joined Maine Foodie Tours for 3 hours of sampling delectables special to the region. From clam chowder to nutty smoothie to Maine’s Needhams chocolate, we had probably 8-9 courses. I was so stuffed after that I could barely walk. Be sure to come on an empty stomach.
Taste beer at a brewery
If you love beer, you will love the microbreweries in Portland. Don’t know which one to pick? Take the Maine Brew Bus tour! This boozy tour will show you around the local craft alcohol scene, with stops in breweries, distilleries, wineries, and bars. I dare you to walk in a straight line when it’s all over. 😉
Go to an Improv show
Fresnel Theater is Portland’s home for improv comedy. I checked out one of the live shows and it was so much fun. Similar to “Whose Line is it Anyways”, the show is a sports match featuring two teams of comedians, who compete in a series of games where they earn points for making the audience laugh. A referee is there to call foul and make things interesting. I was so impressed with how quick on their feet the players could think. They really got jokes for days. I laughed from beginning to end, until my cheeks hurt.
Catch some lobsters
From the first weekend of May to the last weekend of October, you can go on lobstering excursions with Lucky Catch Cruises in Casco Bay, Maine. Try your hands at pulling the lobster traps and learn about the lives of the fishermen (or lobster-men?). The lobsters caught on the tour can be purchased for a discounted price and brought to cook at the restaurant near the harbor. Talk about a real catch of the day.
Watch a sunrise
There is simply nothing like seeing a sunrise over the sea. Since much of Portland’s coast is facing the east side, it’s perfect for catching a sky show in the morning. You have got to be an early riser though. I was at the Spring Point Ledge Lighthouse at 5:30 am and was rewarded with a breath-taking view. I mean, just look at the picture above. Yes, I took this photo.
Day 1& 2 – Where to stay in Portland
Spring Point Inn at the McKernan Center
Spring Point Inn is located on the campus of Southern Maine Community College. It is a unique facility run by students in the Culinary and Hospitality Management program. Only a 7 minutes drive to downtown Portland, Spring Point Inn is an underrated accommodation spot that I don’t believe many tourists know about. I loved my stay here. The ocean was right outside my window and I was able to walk to the beach in 2 minutes.
Black Elephant Hostel
For those looking for a budget-friendly place to stay in downtown Portland, Black Elephant Hostel is very well reputed. Its decors are colorful and funky, giving a very welcoming vibe. The establishment has many shared rooms as well as some private rooms. I did not personally stay here but had heard many good things from friends who did.
Maine Road Trip Itinerary Day 3 – Harpswell to Boothbay Peninsula
Today is the day we get off the beaten path and start our road trip along Maine’s epic coastline. The MidCoast & Islands region is incredibly picturesque with its mountains, beaches, and forests. I got to go on a girls trip here recently and we had a blast discovering some of its hidden gems.
Things to Do Near Harpswell and Boothbay Peninsula
Hike the Giant’s Stairs Trail
The Giant’s Stairs Trail in Harpswell is about an one hour drive from Portland. The dramatic rock formations here are very interesting to see. The hike is short and mostly pretty easy, with some rugged parts. On a lucky day, you can spot harbor seals lounging in the sun. We sadly did not see any but we definitely enjoyed the sight, sound, and smell of Casco Bay.
Grab a lobster roll at Red’s Eats
One cannot visit Maine without eating a lobster roll, and you can find the best one in the whole state at Red’s Eats in Wiscasset. It’s a humble looking little restaurant on a street corner. But it has big fame. Even celebrity chef, Andrew Zimmern, has eaten here! In the summertime, the queue apparently goes on and on. We visited during May and did not have to wait for too long (See, it pays off to travel during the off-peak season!) The rolls we got came with huge generous chunks of fresh lobster on pillowy buns. It was as if Hallelujah started playing when I bit into the buttery juicy goodness. We also tried Red’s Eats fried zucchini, Green Bee Honey Sodas, and Round Top Ice Cream, which were all pretty good as well.
Frolic in Coastal Maine Botanical Gardens
This beautiful garden in Boothbay has something to offer for people of all ages and abilities. The land is nearly 300 acres with trails, lakes, gardens, greenhouses, and more. We got a tour of the grounds from Ellen, a kind volunteer. Some of my favorite features of the park space include:
Lerner Garden of the Five Senses A space where you can experience nature through touch, hearing, taste, smell, and sight. I appreciate that the garden is so thoughtful towards those who are differently-abled. There are even seasonal therapeutic horticulture events where people use plants and gardening to improve their mental and physical health.
Children’s Garden A slice of storybook magic for the little ones. This area is inspired by classic Maine children’s tales. The kids can play in the frog and fish-filled pond, veggie patch, and adorable wood houses. We learned that in the summer, the garden hosts Fairy Fridays, where kids come dressed up as fairies and do fairy-related arts and crafts. I guess I never grew up on the inside because I really want to join this cool party!
Native Butterfly House The butterfly house, opened seasonly, is where you can get up close to some adorable butterflies and moths and learn about their life cycles. Check out Black Swallowtails, Monarchs, Luna Moths, and more.
Join a Boothbay Haunted History Tour
Boothbay has so much history and a fun way to learn about it is by taking a walk with Red Cloak Tours. Sally, the owner and original guide, is so knowledgeable. She shared with us many mysterious stories about Maine’s ghosts and spirits, weaved together with captivating accounts of historical events. We had goosebumps. For those who are easily spooked, there are strictly historical tours as well. 😛
Day 3 – Where to stay in Boothbay Harbor
Topside Inn is an award winning property with titles including #1 Hotel in Maine and the #5 Most Romantic Hotel in the US. We felt really spoiled to stay here. First of all, the rooms are spectacular. You can see the water right outside the window and the interior decors are straight off Pinterest. I fell head over heels for the in-room bathtub in one of the suites. Can you say goals?
The Inn is managed by Buzz and Mark, a lovely couple who goes out of their way to make sure that everything is perfect. It’s clear that their hard work pays off as many guests have returned to Topside Inn again and again.
Lastly, the breakfast at Topside Inn is definitely something to write home about. During our stay, we were treated to a handsome presentation of homemade goodies like granola, fresh English muffin bread, all sorts of whipped butter and jams, cured salmon, and mushroom & gruyere deviled eggs. The highlight though had got to be the buttermilk waffles with cherry bourbon sauce, fresh whipped cream and country sausage. Oh.Em.Gee. I am drooling just reminiscing about this glorious meal.
Maine Road Trip Itinerary Day 4 – Bristol & Camden
Let’s keep driving north! Maine has a jagged coastline with countless peninsulas. Bristol is another one worth stopping by. End the day in Camden, a small town that is a popular summer vacation spot.
Things to do near Bristol & Camden
Have a photoshoot at Pemaquid Point Light
Fun fact, Pemaquid Point Light and its surroundings have been featured as a possible wallpaper in Windows 7. The park really is a photographer’s dream. You can walk down to the rocks, which has been shaped by earth’s forces into layers and folds over millions of years. We took the opportunity to dress up for a photo shoot.
Top tip: capture the stunning reflection of the lighthouse in the water!
Shop at The Good Supply
The Good Supply is a unique store that curates works of Maine artists and artisans. We met Catherine, the friendly owner, who gave us a tour. Set in a barn in Pemaquid, The Good Supply was started by Catherine to cultivate creativity and community. The space oozes inspiration from nature in many ways. There are housewares, toys and all sorts of handmade art pieces that would make great gifts. We could not help but pick up a couple of things because the craftsmanship and quality looked outstanding.
After all, buying from small businesses is a great way to support the local community and a great excuse for shopping. 😛
Take a cooking class at Salt Water Farm
The Salt Water Farm Cooking School is a cozy place to spend an afternoon/evening with good company, as you learn to prepare true farm to table food. Annemarie created her cooking school on a farm in Lincolnville in 2009. Since then, she has built quite a fan base as she teaches home cooks of all levels how to make simple nourishing meals using timeless cooking methods. The class and workshops utilize fresh seasonal ingredients from the garden, surrounding land and sea. As well, the Salt Water Farm cooking school supports Maine’s farmers, fisherman, and craftsmen. Annemarie also hosts class series based on regional cuisines such as Mexican or Parisian, as well as themes honoring iconic chefs such as Julia Child or Edna Lewis.
Maine is filled with inventive entrepreneurs. It was a pleasure for us to chat with them, especially femalepreneurs like Annemarie and Catherine. The businesses they have been able to create through their passion and persistence are incredible.
Explore Camden Town
Camden is a pleasant seaport town with a laid back vibe. It is not only an attractive place to vacation, but many people move to Camden to raise kids and build a life here. In the summertime, the town is always buzzing with excitement. Popular activities including yachting, watching fireworks in the harbor and attending the Lobster Festival in August. In the winter, there is the National Toboggan Championships. What does that entail you ask? Basically, people dress up in hilariously goofy outfits and catapult down an extremely steep slope. Sounds intense? Oh yes, it is. Watch this video to see the race in action.
The town has many quirky boutiques and nice restaurants. I highly recommend having dinner at Long Grain, a delicious Thai food restaurant on Elm Street.
Day 4 – Where to stay in Camden
We stayed at 16 Bay View by the Bay View Collection. I had already thought my room was bougie when I counted 10 pillows on the bed, freaked out over the fireplace (I adore fireplaces), and found a fluffy robe. But soon after that, I realized that I had my own jet tub and the bathroom floor was HEATED. My mind was officially blown. Those following me on Instagram would have saw me dancing around the room like a goof. Couldn’t help it. I felt like Beyonce staying at a place so swanky. 😛
Renovated from an original historic brick building, the interior combines elements of vintage and modern.
Maine Road Trip Itinerary Day 5 – Prospect & Castine
Today, we bid goodbye to the MidCoast & Islands and continue into the DownEast Acadia region. There is so much more to be uncovered in Maine from Maritime Heritage to food and culture.
Things to do near Prospect & Castine
On the Western bank of the Penobscot River, in the town of Prospect, is a historic site called Fort Knox. This is a National Historic Landmark worth paying a visit to. Constructed between 1844 to 1869, it was the first fort in Maine to be built of granite. Its presence has helped protect the Penobscot River, which was weak in defense during the American Revolution and the War of 1812 against the British. Since its construction, Fort Knox has seen two periods of military activities, during the Civil War and the Spanish-American War. It was helpful to have one of the volunteers walk with us around the batteries and share stories about life at the fort for the soldiers. The site is very well preserved. In the summer months, you can even get a nice panoramic view of Penobscot Bay from the observatory on the Penobscot Narrows Bridge, the tallest bridge observatory in the world.
Have lunch in Bucksport
Drive across the Penobscot Narrows Bridge to the little town of Bucksport. Have lunch at Friar’s Brewhouse Tap Room. The restaurant is run by two friars, brother Don and Ken. They are very personable hosts and excellent cooks. We liked that there’s a house rule of no cell phones. The friars want the guests to enjoy a meal where there is no distractions, just good conversations. Must-tries at the venue include the handcrafted beer and lobster Mac and cheese.
Wander around Castine
Finish the day at Castine, one of the oldest villages in North America. Founded in 1613, Castine has been occupied continuously since its existence. From the French, to the Dutch, to the British, everyone sought after this beautiful land surrounded by the sea. Today, as you walk around Castine, you can see Georgian and Federal houses from the 18th and 19th century, still in great conditions. For history enthusiasts, make sure to visit the Wilson Museum on Perkins Street and the Castine Historical Society on the Town Common to learn more about Castine’s past.
For adventure junkies, one of the best things to do in Castine is to rent some kayaks and get out on to the bay. In the summer, you can even take bioluminescence tours where you can see glowing bacteria in the water.
Day 4 – Where to stay in Castine
Those who are suckers for vintage and antiques, like me, would adore Pentagoet Inn. This bed and breakfast is a treasure trove of relics from the past. I felt like we had traveled back in time to a bygone era.
The in-house restaurant offers delicious treats all day. I may or may not have had too many mini cupcakes. For breakfast, we were served yummy pancakes featuring Maine’s famous blueberries.
Maine Road Trip Itinerary Day 6 – Deer Isle
This is our last full day on the Maine coastal route. Let’s see what surprises Deer Isle has in store.
Things to do in Deer Isle
Helen and Scott Nearing are two influential figures in America’s “Back to the Land” and “Simple Living” movements in the 50s and 60s. Their book, “The Good Life”, has taught Americans about home organic gardening, and living a sustainable lifestyle. Helen and Scott were also advocates for social and economic justice. Although the couple had passed away, their legacy continues on at their former home, the Good Life Center. Now, visitors can visit this quaint forest farm homestead to enjoy its beauty and tranquility. As well, the property has a seasonal residency program where participants can stay on the farm, help take care of the gardens and live the good simple life just like Helen and Scott did.
Discover the Unexpected at Nervous Nellie’s Jams and Jellies
Maine definitely does not lack imaginative artists, just like it does not lack nature. Nervous Nellie’s Jams and Jellies is a wacky mini-village nestled in the woods that everyone going to Deer Isle should know about. The name only tells you that it’s a jam shop, but Nervous Nellie’s is so much more. Throughout the premises, you can see quirky sculptures created by owner and sculptor Peter Beerits. Step into the saloon or the juke joint to find “people” on a date or ordering a drink at the bar. We were thoroughly entertained by the artworks imitating life.
At the shop, you can purchase sculptures, other handcrafted goods, and of course, yummy jams and jellies.
Day 5 – Where to stay in Deer Isle
Pilgrim’s Inn used to be a private home in the 1700s and was later converted into a bed and breakfast. Although it has undergone numerous renovations, original historic details of the property have been kept intact. We were welcomed by the inn owners, Nicole and Scott. They immediately made us feel at home. Every room in the inn is uniquely decorated, and always giving a homey and relaxing vibe. The view from the hotel looks out to a stunning pond. I just wanted to curl up with a book near the window and stay there for hours.
Maine Road Trip Itinerary Day 7 – Blue Hill & Back to Portland
Boo! It’s our last day in Maine! Before heading back to Portland, why not explore a little in Blue Hill on the way?
Things to do in Blue Hill
Have breakfast at Sandy’s
Sandy’s Blue Hill Cafe will give you a nice cuppa freshly roasted coffee for those long drives. Their breakfast specialties include blueberry stuffed French toast and homemade fried egg sandwiches.
Visit Blossom Studio & Gallery
This adorable shop in south Blue Hill combines some of my favorite things in life: furry pals, Harry Potter, and jewelry. Blossom Studio & Gallery is run by two sisters, Sihaya and Kipp Sienna Hopkins. Sihaya is a glass artist who makes gorgeous colorful beads, while Kipp is a talented illustrator who loves to paint cats in all sorts of scenarios.
How kawaii are these postcards?!
Drive Back to Portland (or not?)
Well that’s a wrap of our 7 days coastal Maine road trip. From Blue Hill, it takes under three hours to drive back to Portland, where you can catch a flight home.
I hope you liked this itinerary, as I definitely did. Maine is an incredible state. 7 days is honestly far from enough time to uncover all of its riches. If you are in no rush, feel free to spend more than one day at each of the destinations mentioned in this article. Who knows? Once you are seduced by the charm of Maine, you may never want to leave. 😉
Maine Road Trip Itinerary Map
Ready to go to Maine? Plan your trip in 4 easy steps
- Book A Flight: Find the cheapest flights on Skyscanner, my go-to search engine.
- Find A Hotel: Score affordable accommodation on Booking.com. Receive $16 off your first booking with my link here.
- Buy insurance: You never know what may happen on the road. Protect your trip & gear with World Nomad, the best travel insurance company ever. Get a quote here.
- Read up on the best advice: Love a good old fashion guide book. Suggested reading: Lonely Planet: New England’s Best Trips
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