April 17, 2023

One of my favorite solo vacations I’ve ever been on is a trip up the Maine coast, so I thought I’d share my itinerary and some ideas of places to visit along the way. Writing this blog post is going to let me relive this trip, so I can’t wait to share more with you.

Getting to Maine: you can fly into Portland, ME but I decided to fly into Boston so that I could explore as much of the Maine coast as possible. I picked up my rental car in downtown Boston (and saved several hundred dollars by not getting my car at the airport rental car location) in the morning and made my way north. Below is a map of the coast so you can see my entire journey from Boston to Bar Harbor.

Day 1

By the time I got to Maine, it was lunchtime so I stopped by Bob’s Clam Hut in Kittery, which is just over the Maine border (about an hour outside of Boston). This place was highly recommended and it didn’t disappoint. It was an iconic seafood spot and got my trip off to a great start. For this trip I knew I wanted to take Route 1 the entire way up the coast- it takes a little bit longer but is completely worth it for the views.

Ogunquit- this town is quintessential Maine and was a great first stop on my trip. I walked around Perkin’s Cove and had a chance to stop in some cute stores in the village. I really enjoyed shopping in the Perkin’s Cove Pottery Shop and I thought the bridge over the cove made for a great photo opportunity.

Starting at Perkin’s Cove, you can take the Marginal Way, which is a path a little over a mile long that has amazing views. You can get out and explore along the beach or sit on a bench and take in the scenery. This was one of the most scenic views of my entire trip and it’s a must- do activity.

On the other side of Ogunquit is a cute village with some wonderful restaurants and places to stay. You can also access the Ogunquit Beach from this area- this beach is very popular and has nice sandy beaches (something that isn’t found very much in Maine).

Kennebunkport- In the early evening, I made my way up to Kennebunk and Kennebunkport. I stayed at a cool inn called the Kennebunk Inn. When I travel, I always try to find affordable options that are still nice (when I’m not using hotel points) and I thought this was a great place to stay. The inn is only 10 mins away from downtown Kennebunkport, where I had a chance to explore a little and grab dinner at Alisson’s Restaurant. It’s a classic restaurant that’s been in town for a while and it hit the spot.

Day 2

The next morning, I woke up and walked 100 feet from the inn to the cutest little bakery called Boulangerie- a Proper Bakery- highly recommend and I loved that it seemed to be a spot for locals too.

I did a little shopping and exploring in downtown Kennebunkport, which is a wonderful area. I also checked out the Rachel Carlson Preserve (it was a recommendation from a local- I always love to ask people their favorite places) and it was a great, easy hike that allowed me to see a different part of Kennebunkport/Wells that I don’t think many people see. Close to the preserve is Gooch’s Beach, which I felt like was almost a hidden beach. It’s tough to find parking but if you’re lucky enough to grab a spot, be sure to explore this beach for a bit too.

Even though Kennebunkport has so many wonderful shops and restaurants downtown, I would recommend exploring a bit outside of the downtown area too if you have time. You can check out Walker’s Point, which is the summer retreat owned by the Bush family, as well as a few other small islands.

I loved Kennebunkport so much that I have an entire blog post dedicated to this picturesque Maine town. You can find more in the post here and read about a few additional things I did while I was in town.

Early that evening, I made my way towards Portland, with a stop at Cape Elizabeth. I read that the lobster rolls at the Lobster Shack at Two Lights were some of the best around, so I knew that had to be my first order of business. It ended up being a great dinner spot and I loved the scenery just as much. It’s right by the lighthouses so I also got to check out my first lighthouse of the trip. After dinner, I went into downtown Portland just to walk around a bit and ended up grabbing a drink at a local speakeasy, which is always fun.

Day 3

Portland- This was my main day to explore Portland and I knew I had a lot on my to-do list. I started my day with a famous potato donut from the Holy Donut. Then I made my way out to see several lighthouses. There are so many close by, that you can actually do a lighthouse bike tour, but I opted to drive to them instead. The first lighthouse I visited was the Portland Breakwater Lighthouse, known as “Bug Light”. I thought it was the cutest little thing and had some cool detail on it. Then I went to Portland Head Light, which is one of the most famous lighthouses in Maine. In addition to it being a great landmark, they also have a lot of green space and room to let the kids run around. The park also had some food trucks on site (lobster rolls, etc.) so it would make for a good spot to hang out for a few hours.

I made my way back downtown and checked out some of the neighborhoods outside of Old Port (which is the touristy part of Portland). I always like to find the parts of town where there aren’t a lot of tourists, so I highly recommend you do the same when you’re in Portland. I really enjoyed looking at the houses on the East End and thought that the Eastern Promenade and trail along the water in that area were great as well. I also explored Munjoy Hill and thought there were some cool stores and dining options there too.

I toured the Portland Observatory and loved it. The tour guide was very knowledgeable of the history of Portland and it has great views of the city from up top.

As I mentioned, Old Port is a very popular area and there is a reason why- there are tons of things to see and do down there. I would love to especially try more restaurants in that part of Portland but I ran out of time and meals. I was craving Italian food that night and I knew that all of the restaurants in Old Port would be busy so I found an amazing local spot in the Bayside neighborhood called Isa Bistro. I sat at the bar (my favorite thing to do when traveling solo) and the entire meal was perfection.

If you’re in town during the summer, also be sure to check out Thompson’s Point to see if they might have some concerts or events going on while you’re there. I went and drove around the area right after an event had ended and it seemed like a little hidden gem.

After dinner in Portland, I drove about 20 mins to Freeport, where I stayed at a Hampton Inn. There are a handful of restaurants and breweries in this area too. It was the perfect location for my next day’s adventures.

Day 4

Freeport- Freeport is most well known for being the home of L.L. Bean, so even though I don’t have a lot of their clothes, I knew I wanted to go check out their headquarters just to see what it was all about. There are some outlets surrounding the L.L. Bean store, so I took some time to do a little shopping. I really enjoyed the Freeport Market, which was a store that had a lot of local art and items from to Maine. The L.L. Bean store is huge, with several levels and rooms- something for everyone. They even have a home goods store as well as an outdoor discovery program.

After I shopped, I made my way to Wolfe’s Neck Center, which is also in Freeport. I read about Wolfe’s Neck before my trip and wanted to see what it was all about. This place is a non-profit educational/environmental center and has a little bit of everything- they have some great camping spots, trails, farming, etc. I actually rented a bike there and road around the property, which was nice. It would be a great place to take kids so they can see the animals and explore.

Mid-coast Islands- After exploring Freeport, I kept on driving north and drove through the town of Brunswick- it’s very cute with quite a few shops. I then made my way towards what is known as the “fingers” of Maine- i.e. a series of islands and peninsulas that are in mid-coast Maine. I was hoping to do some kayaking that day but it was too windy so they weren’t offering it. I did drive all of the way to the end of Bailey Island and explored Harpswell, the Giant’s Stairs, and Orr’s Island as well. The woman at the kayak shop told me about a cool trail that she liked in Harpswell that can be found at the Bowdoin College Schiller Coastal Studies Center- I really enjoyed it and loved that it was so quiet. The entire area I explored that day was so laid back and not touristy one bit.

Bowdoin College Schiller Coastal Studies Center Trail

The place I booked to stay for this night, I was looking forward to so much and it didn’t disappoint. I found it online and it’s called the Squire Tarbox Inn. It’s located in a remote part of the coast but it was so precious- I almost felt like it would be in a movie. There were only two other guests staying there that night and we all ended up having breakfast together the next morning- it’s that quaint. I can’t recommend this place enough if you’re in the area.

For dinner that night, I went into the town of Wiscasset and ate at Water Street Kitchen and Bar, which hit the spot. I met some great folks while eating at the bar and saw some great views of the ocean as well. Red’s Eats is located right around the corner and is a famous restaurant for their lobster rolls- I didn’t have a chance to get one this trip but next time I will…and you have to get there early because the line was wrapped around the building when I drove by there later.

Day 5

Bath/Boothbay Harbor/Rockland- the next morning I woke up early and backtracked just a hair to go to the town of Bath. It was full of life that day and they had some great shops in town. They also had a farmer’s market on the waterfront, which both the locals and myself enjoyed. After walking around for a bit, I made my way to Boothbay Harbor. I didn’t have time, but I would have loved to have checked out the Coastal Maine Botanical Garden- next time! I was on a time crunch to be in Boothbay Harbor because I had scheduled a whale and puffin watching cruise. This area has several companies that provide those tours, so be sure to check them out if you’re interested. You do need to get there early enough to find a parking spot- it’s very touristy and crazy in Boothbay Harbor so allow enough time to navigate parking. I did see both puffins and two whales on my tour, which was awesome (be sure to bring binoculars to see the puffins) but let’s just say that I didn’t feel great after that boat ride. :) As a result, I didn’t walk around Boothbay Harbor too much and was ready to get back on the road.

I stopped in Rockland to grab some dinner and maybe because I was just really hungry but I loved my crab cakes at Hill’s Seafood Co.- nothing fancy, just how I like it. The town of Rockland is filled with shops and restaurants. After dinner I got to the cabin that I had reserved and I was so impressed. I had trouble finding a good place to stay along this stretch of the coast so I can’t recommend Point Lookout enough. The cabin was nice and spacious and the entire property was great- they even have a soccer field and a gym as well. If you’re heading up to Acadia on a road trip, this is a great option.

Day 6

Acadia National Park- I woke up early and drove about an hour and a half to Acadia National Park. I was really looking forward to exploring this incredible National Park and wanted to make sure I got there early enough to beat some of the crowds. (Side note: I have an entire blog post on my experience at Acadia, if you’d like to read a more detailed description of my time at the park). I knew my first stop was to Sand Beach because I heard that the parking lot fills up early. I continued on throughout the day around Park Loop Road, stopping off at a variety of places. I hiked around Jordan Pond and was actually able to get seat fairly quickly at the Jordan Pond House (only because I was a party of one), but just know that there is usually a line for this restaurant so plan accordingly…but worth it for those delicious popovers that they’re known for.

I also explored some of the carriage roads throughout Acadia for a little while- don’t miss out on this cool feature of the park. These roads are only accessed by foot/bike/horse and are less traveled, which made them feel like they were almost a secret part of the park. I especially loved looking at the bridges on the carriage roads.

I was able to book a reservation to visit Cadillac Mountain in the park, which is the highest point on the eastern seaboard of the U.S. and was really looking forward to the incredible views…but unfortunately the weather was foggy and rainy so I couldn’t see a foot past my hand. Oh well, more of a reason to come back and visit Acadia!

That evening I checked into the Acadia House Inn, which I highly recommend. The owners were so nice, the food was great and it was located in downtown Bar Harbor, within walking distance of all of the shops and restaurants. I really enjoyed walking around Bar Harbor and it was one of my favorite towns on my trip.

Day 7

I had a little time in the morning to go to Acadia National Park again so the day before, I asked one of the rangers what her favorite hike in Acadia was and she said she loved the Flying Mountain trail, which was on a different side of the park. This was the perfect trail and actually got me to a quieter side of Acadia, which I loved. I didn’t even realize, but there are parts of Acadia that you can visit without buying a pass and this was one of those trails. The views were awesome and the trail had a little bit of everything to see/hike. While I was in the area, I also went to the Bass Harbor Head Lighthouse, which is also a popular spot of the park.

Camden/Rockport/Brunswick- After I hiked around that morning, it was time to head back down south. I left this day as a day to visit any spots that I missed when I was traveling north and this ended up being a great plan. I really wanted to walk around the town of Camden because when I passed through there on my way north, it looked so cute…and confirmed, it is such a cool place. Between the shops, the views of the water and the really gorgeous old homes, I fell in love with the town. Make sure you add this to the list when traveling through Maine.

I also was able to see a few lighthouses that I had on my list- I thought the Rockland Breakwater Lighthouse was a unique one so I’m glad I checked that out. I had lunch at McLoons Lobstah Shack and it was my favorite lobster roll of the trip and located back in the harbor. I also walked around Rockland and Brunswick again and checked out a few things I missed the first time around. I thought the pedestrian bridge in downtown Brunswick was neat to see and made for a cool photo op.

If you’re looking to make this a 7 day trip through Maine, I would still try to book a late afternoon/early evening flight home and make sure you allow for time to check out anything you missed the first time around. I do think though that if I hadn’t have done the whale watching tour in Boothbay Harbor, I would have had time to see a lot more on my way up to Acadia so that would allowed for the 7th day for just traveling home.

I actually continued my trip and went to Boston for the evening and then to Martha’s Vineyard for a day so if you have a few more days available for vacationing, I would recommend adding those places to your trip as well. If you need any tips for visiting Boston- check out my blog post here.

Overall, I can’t recommend taking a trip up the Maine coast more- it was an incredible experience and I hope everyone has a chance to visit this part of the country. I know this post is lengthy but hopefully it gives you an idea of places to visit and help you figure out the timing of the trip.

Maine Road Trip Itinerary