A First timers Guide of Maine In The Fall

Are you planning a trip to Maine this fall? It’s incredibly beautiful during the Autumn months, and I’ve got your guide with the best places to go and things to do while you’re there. From shopping, restaurants, and coastal drives this post will go over everything you need to know about visiting Maine In The Fall.

Day 1-Flying into Maine 

There are a few places in New England to fly into. It depends on what specifically you are looking to do but for us, the perfect place to start was Portland, Maine. Since we planned our trip to take place in mid-October, the southern part of Maine would be in peak fall colors at that time. Flying into Portland is easy, it is a small international airport. We chose to fly Southwest because Steve is my free companion and we found a variety of flight options that fit our needs. The airport was clean and efficient, the employees were extremely helpful, and there was even a taxidermy aminal display of various Maine animals on the way to the baggage claim. 

Do you need a car in New England?

Since we knew we were going to be road-tripping around the coast, we opted to rent a car right at the airport. Portland is only 15 mins from the airport and you can easily grab an Uber to your hotel. This may be a good option if you are staying local or want to avoid an overnight parking fee from your hotel. 

As for exploring New England, I would say you definitely should get a car. Technically you can Uber from town to town because they aren’t that far apart but you’ll probably spend way more money doing that than just renting one.

An Afternoon in Portland, Maine In The Fall

Portland is easily walkable, clean, and safe. We stayed in the Old Port District. This area is right on the water with plenty of hotel options, dining, and cute shops. As you walk around the Old Port you can feel the history. Most of the buildings are brick, and some of the streets are still cobblestone.

Old Port has everything from Seafood to Thai and it was all delicious. The famous Gilbert’s Chowder was first on our list and it didn’t disappoint. Located right on one of the piers, Gilbert’s is an old-school eatery. We split the lobster roll and a bowl of clam chowder. Both were delicious and enough for 2 people to share, which is good because lobster rolls are pricey!

After Gilbert’s, we walked down the main street by the wharf. There are plenty of cute stores for souvenirs, art galleries, and clothing stores. Each one had its own charm and style. Two stores that we recommend stopping into are Blanche+Mimi and LeRoux Kitchen. 

Blanche+Mimi in Portland, Maine

Blanche+Mimi is filled with all types of items. Not like an antique shop but not like your typical home decor store. Each item felt unique and was selected for just the right feeling. I would have purchased one of everything if I could, there were so many great choices.

LeRoux Kitchen is more than just the usual jams and jellies tourist shop. It has so many unique items that were not only functional but also provided a New England flair. Tastefully designed lighthouse salt and pepper grinders, utensils for eating shellfish, and of course the multitude of tea and coffee mugs. Steve has a weakness for kitchen stores so of course he poked around in every corner before we could move on. 

Heading up a cobblestone street we stopped at Henry’s Public House. This moody restaurant/ bar was just the spot to wait for our reservation at Via Vecchia. Henry’s offers great cocktails and food along with live music. 

Via Vecchia in Portland, Maine

Finally, the main culinary event, Via Vecchia. This place was top-notch. Centrally located in Old Port, this restaurant is a real gem. Housed in a beautiful brick building with large beautiful iron-clad windows, Via Vecchia’s food was as good as its atmosphere. We had the carpaccio, burrata, and mussels. Everything was amazing, and the service was exemplary. I will be dreaming of this food for years to come! They even have a complimentary coat check, which we’re not used to being from San Diego or Nashville. Definitely make a reservation here!

We stayed at the Cambria Hotel which was within 10-minute walking distance to Old Port. It was nice and the staff was helpful, but the walls seemed to be a bit thin. We could hear other guests snoring and walking around all night.

*Some tips for Portland* Don’t go on Tuesdays and Wednesdays- most stores are closed. Although there was plenty to see and do, we were disappointed to not be able to visit the Allegash Brewery and some boutiques.

Day 2: Driving up the coast of Maine in the Fall

The next morning we walked down the street to the Standard Barkery for breakfast, there you will find artisan breads and well-crafted pastries. Don’t be intimidated by the line, it moves quickly and is well worth the wait. We had the pear tart, the chocolate croissant, and the morning sticky bun. They were all absolutely amazing! *Tip- If you are a latte person, like me, grab one before you go because the Standard Bakery doesn’t have them.

After breakfast, we were ready for our road trip up the coast. We headed to Freeport, Brunswick, Bath, and Booth Bay. Now would be the time to pick up your rental car and if you are leaving from Old Port, we suggest getting some Standard Bakery treats to go on the road.

Freeport, Maine in The Fall

The first stop was Freeport, Maine. This is only 30 minutes north of Portland. This town is an outlet mall disguised as a cute little town. Don’t get me wrong, the LL Bean headquarters was definitely worth the stop but be ready for a lot of name-brand outlet stores, and camping-style stores like Patagonia.

Fun fact about the LL Bean store, it’s open 24/7! They had a little trailer serving delicious coffee before we went to take photos with the giant boot out front. The store is massive! Steve and I parted ways and went to separate floors to look at clothes and items. The shoe wall upstairs was incredible! We bought a jacket for me and Steve got his first knit cardigan. He’s worn it almost every day since we returned home! LL Bean is absolutely worth a stop.

Freeport does have some great local boutiques offering everything from art and furniture to jewelry and home goods. We ate Linda Beans and split another lobster roll and Caesar salad. This lobster roll was better than the one at Gilbert’s and was enough food to keep us going. If you can tell, there is going to be something to eat around every corner in Maine. Things can be pricey so sharing is a great way to try a lot of food without being totally stuffed all day. 

Brunswick, Maine

Brunswick was the next town that we passed through. Although we didn’t have time to stop, it is a really cute town. Larger than the next few that we visited but could be a good place to stop if you have a little one that needs to get out and run around a bit. Brunswick had a large green space/ park in the center of town that was close to shops and stores. We even saw a few food trucks there as we passed by.

Bath, Maine

We weren’t planning to stop in Bath but decided to try and find me a sweatshirt that said Bath (I love baths haha). Although we didn’t find one, we did find a great coffee shop with excellent apple cider and homemade pastries. Bath is really small but SO cute, and a great stop to get out and stretch your legs. The riverfront has a beautiful tree-covered park that was showing off its fall colors. There were chairs and tables and great views of the river.

Boothbay Harbor

Last but certainly not least was Boothbay Harbor. It was nearing the end of the day when we arrived but that was perfect. There were still a fair amount of shops still open and the last of the tour groups were making their way back to the busses. Boothbay was all ours.

This little fishing village on the harbor is exactly what you are picturing in your mind. A little hillside covered with tiny shops leading down to the bay. In the bay is a walking bridge that stretches 1000ft, from one side to the other. The views from the center of the bridge are breathtaking!

The bay opens towards the southwest, so the setting sun sets a beautiful sky that is reflected in the water. The smell of the salt air, the cool breeze, and a lovely New England view in every direction. This was our favorite stop of the day. It was stunning! I wish we started here and ended in Freeport.

There were these beautiful homes along the street by the water. Such a quaint town!

After Boothbay, we drove back to Portland.  We ate at Dok Mali, a local Thai food restaurant and it was delicious and fresh. Steve had a rice noodle soup and I had the drunken noodles- If you like Thai food you’ll love this place.

Day 3: Drive down the coast of Maine to Boston

We checked out of our hotel and headed to the infamous Holy Donut. It was ok, but not a must-see, in my opinion. I’d stop at Standard Bakery again instead next time. On our way out of town, we stopped at the Portland Head Lighthouse. It is a beautiful example of a New England Lighthouse that is super accessible by car. The drive to the lighthouse is pleasant and you can see plenty of New England-style homes surrounded by fall leaves on the way. The lighthouse is surrounded by a large park, with ample paid parking. If you are planning on spending a significant amount of time here it may make sense to Uber rather than drive.

The lighthouse offers great views of Portland, the bay and the surrounding coastline as well as views of the lighthouse itself. The park is built over the top of a WWII Fort, and one of the Garrisons is still visible. With so much space the park is a great place to get away from other folks and take in the beauty of the Portland coast. 

Kennebunkport, Maine in the Fall

Our goal for the third day was to take in as many of the coastal towns between Portland and Boston as we could. The first stop was Kennebunkport which was by far the most fun village that we visited. Kennebunkport is a must-see! Parking was a bit of a challenge but the town was worth it.

The downtown area is so cute, they have the usual candy and coffee shops but the more you peeked into places the more you found unique gems. Then we walked down to a bridge that went over the river and ran through town.

They had the best fall pumpkin display- we had to get a photo!

Ogunquit, Maine in the Fall

Next Stop was Ogunquit, Maine. This is a really cute beach town. The downtown itself is set back from the beach with plenty to see and do. The town does have beach access and paid parking, We managed to get down to the sand for a quick stroll.

There we saw all these older folks soaking up the sun even though the sea air was pretty cold. I think this would be an amazing town to see in the warmer months in Maine. Ogunquit had a lot of shopping and restaurants. It’s a really cute town but it was packed and after driving around for 15 minutes looking for parking we decided to move on.

After Ogunquit, we stopped for lunch at the famous Bob’s clam hut. Apparently, they have the best fried clams. So far these are the only fried clams we have ever had and we are not so sure we will be getting them again haha. They were a bit pricey but the clam hut was a good stopping place to stretch before moving on to Portsmouth, New Hampshire. 

Portsmouth, New Hampshire in the Fall

Portsmouth is AMAZING! It had a very historic feel and was surprisingly large. Walking around the downtown area was really fun.

They had the best shopping out of everywhere we saw so far. Lots of boutiques, restaurants, and more. It was a nice break from the car.

After popping into a few places we had a Kilwins Carmel Apple. We have Kilwins in Nashville too but we just couldn’t resist. 

That’s all for our trip to Maine in the Fall! We continued on to Boston and Salem and spent a total of 5 days in New England- it was a greaet trip and we can’t wait to go back!

I hope this post was helpful for you to find fun things to do in this picturesque part of the country. Don’t forget to check out some of my other travel blogs! If you’re into traveling, these blogs are super helpful!

The Best 3-Day Northern Oregon Coast Road Trip

A First Timer’s Guide to 3 Days in Charleston

10 things to know about Secrets Moxche in Playa Del Carmen

xx,

Lauren