The Best 5 Day New England Itinerary 

If you’re looking for the best 5 day New England itinerary you’re in the right place. My husband and I went on an amazing 5-day trip to Maine, New Hampshire, Salem, and Boston. We wanted to go in the Fall to see the foliage and cute New England towns. It’s safe to say New England does not disappoint! If you’re hoping for that Hallmark Movie, and Gilmore Girls vibes New England is the place to visit. Picture small towns covered in red and orange leaves, warm meals in cozy restaurants, historical stops, and of course shopping. It’s the perfect vacation!

This post will cover the best 5-day New England itinerary. Where to fly into, where to stay, what to do, & more!

Something to note before we get too far into all the things. If you are looking for great Fall colors, be sure to look at the weather in New England in the Summer. The Summer of 2023 had more rainy days than the usual New England Summer. This causes the leaves to retain their green longer into the Fall season and creates less vibrant colors in the Fall. Although this happened to us this year we still feel that we saw plenty of beautiful fall foliage but it is something to be mindful of if you are planning hikes or specific activities that are aimed at seeing the best fall color. 

Keep reading to learn about The Best 5 Day New England Itinerary!

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. 

The Best 5 Day New England Itinerary 
Look at the fall foliage!

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.

The Best 5 Day New England Itinerary 

The Best 5 Day New England Itinerary 

Day 1 of The Best 5 Day New England Itinerary- An Afternoon in Portland, Maine 

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 buildings are brick, and some of the streets are still cobblestone.

The Best 5 Day New England Itinerary 

If you are anything like me, you will want to taste everything. 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!

The Best 5 Day New England Itinerary 

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 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. 

The Best 5 Day New England Itinerary 
Blanche + Mimi in Portland Maine is a must visit!

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. 

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!

Via Vecchia Portland Maine
The carpaccio at Via Vecchia is incredible!

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 of The Best 5 Day New England Itinerary- Driving up the coast of Maine

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.

The Best 5 Day New England Itinerary 
How cute is the Standard Bakery?

After breakfast, we were ready for our road trip up the coast. We were 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

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.

The Best 5 Day New England Itinerary 

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 definitely worth a stop.

LL Bean's boot wall is a must see
LL Bean’s boot wall is a must-see

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. 

The Best 5 Day New England Itinerary 

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. 

The Best 5 Day New England Itinerary 

Bath, Maine

Bath, Maine
I loved Bath!

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.

The Best 5 Day New England Itinerary 
This is the lovely park in Bath.

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.

The Best 5 Day New England Itinerary 

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 Best 5 Day New England Itinerary 

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 beautiful 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!

The Best 5 Day New England Itinerary 

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 of The Best 5 Day New England Itinerary- 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, then 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. 

The Best 5 Day New England Itinerary 
Portland Head Light House

Kennebunkport, Maine

Our goal for the second 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 Best 5 Day New England Itinerary 

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 the bridge that went over the river that ran through town.

Kennebunkport, Maine
We purchased some really unique things at the Whimsy Shop in Dock Square.

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

The Best 5 Day New England Itinerary 

Ogunquit, Maine

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.

The Best 5 Day New England Itinerary 

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

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

The Best 5 Day New England Itinerary 

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.

The Best 5 Day New England Itinerary 

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

Newburyport, Massachusetts

Next up was Newburyport, Massachusetts. This town was more what I pictured with thinking about a New England town. Rows of cute brick buildings and cobblestone streets. There were large open areas and the intersection of different streets meant there was always something new to see around every corner. Getting to Newburyport was charming in itself. The road in winds past perfectly maintained New England homes. This is when the falling leaves and the autumn colors would be absolutely perfect. They had a lot of cute restaurants and shops to explore plus a beautiful park on the water.

The Best 5 Day New England Itinerary!

Boston, Massachusetts

Finally, we drove into Boston, Massachusetts. Well, crawled really. Up until Boston, there was little to no traffic the whole way down the coast. The last 5 miles took almost an hour to get through. It was excruciating. However, once in Boston, walking and the Subway/ Train system make it extremely easy to get around. I suggest turning your car in early if you plan on staying in Boston for the remainder of your trip. This will also save you nightly parking fees.

The first night in Boston we went to a Haunted Pub Crawl tour. This was a fun way to shake off the day and see a few of the historic sites of Downtown Boston. We booked it with Nightly Spirits and Lucy did a great job telling tales of the haunted city. The best place on the tour was the speakeasy inside the Carry Nation Bar. Although, more restaurant than a Speakeasy, it was a definite vibe with great cocktails. 

Getting back to the hotel that night, we were acutely aware of how different the city was than the surrounding areas. There was tons of road noise, people laughing and shouting, and the ever-present car horns and emergency sirens.

We stayed at Revere, as in Paul Revere. The hotel was centrally located and had easy access to the train lines and trolley stops. It is also close to the Boston Commons and has tons of great places to get a bite to eat. Our two favorites while we were there were Tatte and The Thinking Cup. The Tatte has multiple locations across the city, and although it is a little pricey the food is delicious. The Thinking Cup was less expensive but offered a warm inviting environment. The food there was excellent and really made us feel comfortable when the Nor’easter storm brought the rain in. 

Day 4 of The Best 5 Day New England Itinerary- Salem, Massachusetts

I was so excited for Salem! We started the day walking to Tatte and having breakfast. Then we hopped on the subway to the train to Salem.

Salem is extremely popular in the fall, so think of this more as a country fair than a quiet witch-infested New England town. We decided to avoid the traffic and parking and take the train up to Salem. This was super easy and affordable. For around $20 per person, you can go from Central Boston to downtown Salem. Everyone knows why you are going there and is happy to help you make sure you get to the right stop. The train schedule is posted everywhere in the station. Once off the train, you are directed from the Salem Train Station to the Street Fair. They block off several streets in downtown Salem in October. 

The streets are filled with tons of fans dressing in costumes and Halloween attire. The people watching is pure gold. Everywhere you look there is some ghoul or goblin having a good time. There are magicians and street performers. In the Salem Common, there is fair style food trucks serving local favorites like apple cider donuts. There are several witch museums and paid exhibits that you can tour throughout the day. 

How cute is this storefront in Salem?
The inside was really cool as well!

We opted to take the local Salem Trolley Tour. This is the best way to see Salem! They do a great job pointing out the new and old landmarks and helping to provide the history and the context for why they are significant. Salem is much larger and has a lot more to it than the witch trials. We would have never known if we didn’t take this tour!

A few notable things we learned- The Parker Brothers and their board game factory is in Salem, the first millionaire in America created his wealth in Salem and several famous pirates called Salem home. We would highly recommend the Salem Trolley Tour!

Speaking of tours, there is a constant stream of ghost and witch tours happening all over the city. There are so many that you can overhear the same story with varying degrees of detail just by walking around.

Since we thought of Salem as a sleepy little town and thought it would be fun to take a night tour. It wasn’t… lol. There are so many people and so many tours that the night tour wasn’t any more scary or spooky than the day tours it was harder to take pictures and see the details of the buildings and the witch trial victim memorials. We would recommend taking a tour during the day, then you can still have time to poke around in your favorite spots for a closer look at those historical sites. 

We walked almost 20,000 steps in Salem, and it started to rain as the night set in. Our comfy waterproof shoes and rain jackets came in handy. 

Day 5 of The Best 5 Day New England Itinerary- Downtown Boston

Boston is similar to New York in that there is so much history packed into such a small area! Unfortunately it rained during our entire day in Boston but it was kind of fun!

We opted for the Hop On Hop Off Boston Trolly tour to help us get an overview of the area. Although the Tour was VERY different than the Salem tour, it did get us to a few new areas throughout the day. All in all, it costs less than taking multiple Ubers to get around the city. We had 3 tour guides and one was incredible! What’s nice is you can hop off if you don’t like one guide and grab the next trolley to see if the new guide is any better.

The Best 5 Day New England Itinerary!

Our favorite areas of Boston were Beacon Hill and The Waterfront towards the North End.

It was pouring so we stopped into Quincy Market. This was a massive food hall and shopping mall and is surrounded by modern stores like Sephora, Loft, and Urban Outfitters. If you head across Atlantic Ave, there is Christopher Columbus Park and The Greenway. The Greenway is a series of parks that stretch down Atlantic Ave.

At the very end, there was the coolest Merry-go-Round, except the traditional animals were exchanged for native Boston animals. 

We had lunch after Quincy Market at the Green Dragon Tavern. The Green Dragon Tavern was considered to be the headquarters of the American Revolution. This is where Samuel Adams and the Sons of Liberty frequently met leading up to the revolution. 

The Best 5 Day New England Itinerary!

The tour traveled around the North End and over to Beacon Hill. Beacon Hill is also known as Antique Row. In fact, The buildings on Charles Street in Beacon Hill are federally protected historic sites. This means that they can never change what the outside of the buildings looks like. It almost feels like you stepped onto a movie set. There are so many shops and stores to pop in and out of and of course, a Tatte Barkery to get a coffee to keep you going. One of the more interesting shops we went in was the Beacon Hill Books & Cafe. The Cafe is downstairs and to get to it you have to walk down this tiny corridor in the building. It felt very much like a scene from Harry Potter. The bookstore is above the cafe. It was so fun exploring these little gems. 

I’m usually not a huge antique or fine china person but Elegant Findings Antiques in Beacon Hill changed me! They had the most incredible collection of stunning china I have ever seen! This is a must-see!! The owners are so sweet too- they’re an older couple and seem to truly love what they do. They taught me a lot about different types of china and where it’s from, what makes each piece special, etc. Such a wonderful store!

We finished our trip by having dinner at the famous Union Oyster House! The Union Oyster House is one of the oldest restaurants in the US. Many famous people have passed through its doors, one of the most notable being John F Kennedy. He frequented the restaurant so much that he had his own table, #18. We made a reservation and I’m glad we did! They were packed!

We flew out of the Boston Logan airport and it was an easy, drama-free experience. We had the best time in New England and can’t wait to go back!

I hope you enjoyed this post about The Best 5 Day New England Itinerary!

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the best 5 day New England itinerary

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