Visiting New England has always been my dream, especially during the fall. Last year, we decided to make this dream a reality and made the ultimate road trip from Boston, Massachusetts all the way to Bar Harbor, Maine. Went spent five amazing days in New England during the cozy fall. In this guide, we will give you a step by step itinerary so you can do the same road trip this year!

Our Itinerary at a Glance

Day 1
  1. Fly into Boston
  2. Settle in and have a good night's rest
Day 2
  1. Pick up a rental car and explore the suburbs of Boston in Everett
  2. Stop in Portsmouth, New Hampshire for a delicious seafood lunch
  3. Exploring in Kennebunk, ME
  4. Dinner + Airbnb in Portland, ME
Day 3
  1. Breakfast at a yummy potato donut shop in Portland
  2. Visit the cute coastal town of Camden, ME
  3. Arrive in Bar Harbor, ME & explore the town at night
  4. Stay the night in the coziest motel in Bar Harbor
Day 4
  1. Start your day with a gorgeous local breakfast spot
  2. Wander around Bar Harbor during the day
  3. Rent eBikes and ride to Acadia National Park
  4. Explore Southwest Harbor
Day 5
  1. "Sunrise" hike at Cadillac Mountain (but it was super cloudy)
  2. Lunch in Portsmouth, NH
  3. Flight home to Phoenix!

Here is a map of the trip so you can picture where you will be in New England!

Screenshot of Google Maps showing the road trip route from Boston, MA to Bar Harbor, ME
Road trip from Boston, MA to Bar Harbor, ME

Day 1 : Flying to Boston

Thursday, October 20th, 2022

Flying from Phoenix to Boston with a beautiful sunset!

We started our journey in Phoenix on a Thursday and caught a flight to Boston around 4pm. The flight from Phoenix to Boston is about 5 hours so we took a nap and watched a little bit of Netflix!

Once we arrived in Boston, we went straight to our Airbnb. It was in a convenient location because it was within walking distance from the airport! We got there around 12:45 am, so we decided to get food and before calling it a night. For dinner, we ordered to-go food from Dumpling Palace from DoorDash. They happened to forget the bao balls but the crab rangoons were yummy and so was the orange chicken. Then we went to bed to get some rest for the next day!

Day 2 : Road tripping from Boston to Maine

Friday, October 21st, 2022

Our first morning in New England, we slept in because of the time zone change and woke up in Boston at 10am. We took our time since it was a vacation! We left our airbnb at 11am to Uber to pick up our rental car.

We booked our rental car through the company Getaround and it was very convenient - definitely recommend this company!

From here, we took drove around the cute suburb of Boston in Everett to find our first coffee shop of the trip. We stopped at the Well Coffee House and it was a solid 8/10. They are a non profit and donate the money to community partners. Love their mission! We took our coffee and sat in a peaceful park nearby. It had a cute gazebo and gorgeous hydrangea flowers!

From Everett, we started our road trip to Portland, ME which is where we would spend our second night. This drive was about 1 hour and 45 minutes but we made some stops along the way!

Stop #1: Lunch in Portsmouth, New Hampshire

Our first stop was in Portsmouth, New Hampshire for lunch. Fun fact, Portsmouth is actually pronounced Ports-Smith and is one of the oldest cities on the coast!

We had our first seafood lunch at Row 34, and ever since, we've been obsessed with East Coast seafood. We ordered their shrimp, crab claws, calamari and a king salmon maple belly tartare dish. They had a great selection of oysters too so we had to order some of those!!

We honestly loved all of it and would order the same thing again!

After lunch, we walked the Main Square in Portsmouth and window shopped! They have some really cute and fun stores to look in. We loved 20 Below Boutique and Drift Collective. Drift Collective, pictured on the left below, is an awesome re-mastered shop with fun designs. They have a lot of fun girly gifts too with a lot of attention to female owners and WOC.

After the cute shops we came across the Music Hall - I loved that it's a bright pink building!

Eventually we came across this beautiful old church called North Church, and found out it was established in the 1600’s! It’s a tall white spire and can be seen from everywhere!

North Church in Portsmouth, New Hampshire

I have a big sweet tooth so I knew I had to try out an east coast bakery. We came across Ceres St. Bakery and it was top notch. We had a croissant and a lemon ricotta cookie. The lemon ricotta is a classic Italian sweet and very popular on the East Coast - 10/10. We wish we got more than 1!!!

Lacy Cain Baranack smiling with her pastries outside of a cute and cottage style family owned bakery in Portsmouth, NH.
Ceres St. Bakery had the cutest cottage vibe!! You need to stop here on your road trip.

For our 2nd coffee of the day, we went to this German pastry and coffee shop called Kaffee Vonsolln which had a cool mural inside that made it feel like we were leaving the US and entering Germany! The coffee here was tasty but they had limited flavor options.

The outside of the German coffee shop "Kaffee Vonsolln" in the streets of Porstmouth, New Hampshire
Super unique German café in Portsmouth, NH

After exploring the cute town of Portsmouth, we walked to the Memorial Bridge for a beautiful view of the Piscataqua River and our first look at Maine. I was loving all of the water surrounding us, especially as an Arizona desert girl!

Calm deep blue waters on the Piscataqua River with colonial style homes in the distance and a view of Maine from the Memorial Bridge in Portsmouth, New Hampshire
View of the Piscataqua River and Maine from the Memorial Bridge in Portsmouth, New Hampshire

Stop #2: The city of George Bush's summer home

From Portsmouth, we drove along Route 1 which is the coastal highway here. It’s lined with tiny towns with foreign names I can’t pronounce but they were all so gorgeous! My favorite places I passed were Ogunquit and Kennebunkport.

There was a nice man on our plane named Keith who told us how antique stores are huge in Maine, so we stopped in one just outside of Kennebunkport. Ian found the Rush vinyl record “2112”so we bought it! He loves his music so this was a great find.

Colorful directional street signs on arrows in Kennebunkport, Maine
The streets of Kennebunkport, Maine

After the antique store, we were recommended to go to George Bush’s summer home city in Ogunquit. I saw this super unique antique set that was out of a tea party. Ian's mom would have loved it! My mom didn’t text me back about it lol.

Full white tea set with pink and orange flowers in Ogunquit, Maine
My dream tea set we found in Ogunquit, Maine

Stop #3: Kennebunkport, Maine

Kennebunkport was a darling town in every way! The coast was gorgeous and we couldn't get enough of it. Finding and paying for parking is the only annoying part of traveling on the East Coast. Nothing is free 🤯

Next to our parking spot, there was this beautiful white church with a stunning bright orange tree in front! This family was walking in at the time, ready to get their daughter/son married - love seeing cute moments like this :)

A large tree with vibrant orange leaves in front of a white church in Kennebunkport, Maine
My favorite tree from this whole trip

As we walked along the river in Kennebunkport, we stopped in a darling candle store with starfish hanging from the roof as decor. Pricing was excellent for being in Maine!

Woman smiling during golden hour on an old and rustic bridge over a lake in Kennebunkport, Maine
Walking along the water and over an old bridge looking for a mead shop that apparently wasn’t built yet

Stop #4: Kennebunk, Maine

For our first brewery of the trip, we stopped in Kennebunk and checked out Batson River Brewing and Distilling, which is a chain here in Maine. It was awesome!!! Their happy hour had $5 draft beers which we loved. Their food looked really good too but we passed since we weren't hungry.

An outdoor patio with a large fire pit at a brewery in the town of Kennebunk, Maine
Views from Batson River Brewery in Kennebunk, Maine

After relaxing at the brewery, we wandered back to our car so we could get make it to Portland for dinner. We left around 4:40pm so we had good timing! We only had about a 1/2 hour drive left from Kennebunk.

Stop #5: Portland, Maine

Portland felt like a bustling city when we came in! They have a Seattle/San Francisco vibe with steep hills, “foodie stops”, lots of breweries and cobble stone streets.

A woman smiling with her hands up in excitement during her first trip to Portland, Maine in front of City Hall
Taking a moment to feel the energy in Portland!

Our Airbnb here was AWESOME. We stayed in the basement of a family’s home and it was about a 10 minute drive from downtown Portland. The room was huge with a queen bed, lots of desks, a foosball table, and a bathroom with heated water. Our host even left 2 water bottles in the fridge which was super appreciated.

Now it was dinner time!!! We were hungry for lobster 🦞 Upon Keith’s recommendation, we went to Highroller Lobster and splurged!!!

Ian got a lobster grilled cheese and lobster roll (4oz) with a draft beer. I got a “lucky 7” oyster set (pretty damn good cocktail sauce), a shrimp cocktail and a lobster roll. This restaurant was unique because they’d let you pick out your sauce and we both decided on the jalapeño lime sauce. DELISH!!! But expensive af.

After dinner, we walked around downtown Portland for a bit before heading back to our Airbnb to get some sleep!

Day 3 : Roadtrip from Portland to Bar Harbor, Maine

Saturday, October 22nd, 2022

On our third day into our road trip tour of New England, we wanted to have a quick breakfast in town before we headed north for Bar Harbor.

The first place we saw was The Holy Donut so we new we needed to check it out. They serve delicious gourmet potato donuts - I had never heard of potato donuts before! Apparently these are super popular here in Maine. We had the maple bacon and blueberry and they were SUPER GOOD!

Ian was looking for a breakfast with a bit more sustenance, so we checked out another bakery since our first encounter with East Coast bakeries had us addicted.

Some locals last night at Highroller Lobster recommended us to try Tandem Coffee Roasters, so we went there and they were crazy busy! The line was legit out the door and going onto the sidewalk, but was absolutely worth the wait.

I had the biscuit with jam and Ian had a biscuit with egg, cheese and chorizo. This breakfast was awesome and a great way to fuel our day! I don't know what's going on out here on the West Coast, but these East Coast bakeries we keep visiting are just out of this world!

A perfectly flakey biscuit with egg, cheese, and chorizo, wrapped in foil, for breakfast in Portland, Maine
Yummy biscuits for breakfast from Tandem Coffee Roasters in Portland, Maine

After breakfast, we walked back to our Airbnb to check out and then started our drive to Bar Harbor, which is about a three hour drive north.

Stop #6: Camden, Maine

Our friend from the plane also mentioned for us to visit Camden, so we obviously needed to check it out!

Camden is a cute seaside town with gorgeous views. When you look one way, you’ll see the vast expanse of the Atlantic Ocean with close islands scattered on the horizon. When you look the other way, you’ll see the dense forest of multicolored trees.

It's an amazing thing to see for someone like myself who is from Arizona! Experiencing Flagstaff or Pinetop and being in those very forested areas is a very different feeling from the East Coast forests.

View of boats docked in a marina on dark blue water with an island in the distance in Camden, Maine
Taking in the fresh ocean air from Camden

We found parking right next to St. Thomas’ Episcopal Church with a vivid bright orange tree right outside so I had to take some super cute fall pictures! Afterwards we walked around the town looking for a spot to eat.

Girl smiling while holding a fallen red maple leaf during the fall in Camden, Maine
Embracing the fall weather here in Maine!

We decided on lunch at The Waterfront. The views here were absolutely breathtaking. The food unfortunately did not match the views, especially for the price.

View of boats docked in a marina in Camden, Maine with fall trees surrounding the water
Our lunch view from the Waterfront in Camden

After lunch we wanted to walk around the town a bit more, and ended up getting coffee at Zoot Coffee right off Elm Street. Then we went next door to French and Brawn Marketplace for some fresh apple cider! Definitely check this little market out - it's so cute and has been around since 1868! Then we got back on the road to continue on towards Bar Harbor.

Stop #7: Bar Harbor, Maine

Our first stop in Bar Harbor was the Bar Harbor Motel so we could check in and get situated. The Motel was SO CUTE!!! I was honestly so surprised how clean and spacious our room was. There was also a tree swing right outside our room which was super fun to swing from, I felt like a little kid again.

Something we noticed immediately in Bar Harbor is that everything here is lobster themed! When we entered our motel room, the room service even set up little red towels folded to look like lobsters!

A red towel folded to look like a lobster, displayed on a bed in a motel in Bar Harbor, Maine
The cutest towel display I've ever seen

After we got situated, we drove around the southwest harbor to catch the sunset on the horizon of the ocean. We parked in the area right before the Mount Desert Oceanarium and walked around the rocks near the docks. A kind stranger offered to take our picture, it was perfect!

A couple smiling in front of a peaceful orange sunset on the harbor in Bar Harbor, Maine
Shoutout to the nice girl for taking our picture!!

We were getting super hungry after watching the sunset, so it was off to the heart of Bar Harbor to find some fresh lobster!

There are so many places to eat around the area so it was really hard to decide.

One of the places that really caught our eye was Galyn's! The area was super busy at the time so I quickly dropped Ian off to get a reservation, but he forgot his phone in the car so I panicked, parked and went to find him. Luckily he was in the general area so the crisis was averted!

While waiting for our reservation at Galyn's, we went to the Atlantic Brewing Company for a beer. These two spots are about a 4 minute walk from each other so it was super convenient.

Spoiler: we ended up at these two places two nights in a row because we loved them so much! The first night at Galyn's, I tried crab cakes for the first time and OMG they were so good! We also had the cutest blueberry and lobster themed dessert. Look how adorable!

A slice cheesecake topped with lemon zest, sitting next to a lobster made out of blueberry juice
Dreaming of this cheesecake with the perfect amount of lemon and blueberries!

After dinner, we walked around and browsed through the gift shops and ended up getting more desert at this amazing fudge shop, Ben and Bill's Chocolate Emporium. They have everything from ice cream, candies, fudge, and a new sweet I've never heard of: buttercrunch!

Then, we explored Agamont Park, the Bar Harbor Inn, and the docks looking out at the ocean.

At night, Bar Harbor is a very romantic place to be. Staring out into the harbor with the lights reflecting on the water, I can't imagine a better place to be during the fall!!

View of Bar Harbor at night, with lights from the businesses reflecting on the water.
Bar Harbor, Maine at night

Day 4 : Acadia National Park & More Lobster!

Sunday, October 23rd, 2022

The Bar Harbor motel was super cozy so we slept in a bit. When we finally rolled out of bed, we started our day with a much needed coffee at Acadia Perk and then had breakfast at Cafe This Way. We coincidentally went here on their last day open of the season.!

We learned that at a certain point of the year, most of the town closes down since it starts getting too cold. This is so interesting because the opposite happens in Arizona. Places will close early because it gets too dang hot!

After breakfast, we wanted to wander more of Bar Harbor since it was daytime so we walked south down Main Street and found the Ivy Manor Inn. This place is incredible - I mean look at the bright red ivy leaves covering it! It's straight out of a fairytale.

A woman sitting at a coffee table outside of an old inn covered in red ivy leaves in Bar Harbor, Maine
Lacy enjoying the New England fall vibes in front of Ivy Manor Inn.

Stop #8: Acadia National Park and Southwest Harbor

After strolling through town, we drove to Island Bike Rentals to rent ebikes. We took our ebikes and cycled to Acadia National Park to explore the Southwest Harbor!

Man smiling next to his ebike on the side of the road, cycling to Acadia National Park, Maine
On our way to Acadia National Park!
A couple smiling and standing on giant rocks in front of the Bass Harbor Head Lighthouse in Maine
The Bass Harbor Head Lighthouse!

Cycling up thru Seawall, we discovered Charlotte's Legendary Lobster Pound, and this place is truly a gem. It seems that this is every locals favorite spot as they normally spend hours here each day, and Charlotte even says when tourists come, they come every day of their vacation!

When we got back to Bar Harbor, we stopped at Geddy's Seafood Restaurant for a late lunch.

By the time dinner came around, we were craving Galyn's again, so we made another reservation and then killed some time at our favorite Atlantic Brewing Company.

For dinner this time, we tried their sautéed scallops and of course their lobster. And we finished off we their homemade blueberry apple crisp for dessert!

After our long and adventurous day, we drove back to Bar Harbor motel to get some rest for our early day on Monday!

Day 5 : Cadillac Mountain Sunrise & Back to Boston

Monday, October 24th, 2o22

On our last day in New England, we woke up super early around 5am to hike Cadillac Mountain for the sunrise. However, when we got there it was super hazy, windy, and COLD! I guess that's New England in the fall for ya.

Unfortunately, since it was so hazy there was no visibility, so we didn't get any cool views. It was still worth the experience with the drive up and challenge that we endured!

Though on the way down, we were in for a nice treat because we started to drive below the clouds and saw the gorgeous fall trees throughout the mountain!

After our hike, we got coffee and breakfast at Choco-latte Cafe. This place was absolutely life saving after the hike we just had! Then, we started our journey back to Boston so we could catch our flight home to Phoenix.

We stopped in Portsmouth for lunch again and had a sandwich from Bennetts Sandwich Shop and picked up a juice from The Fresh Press.

Finally, we made it to Boston, dropped off our car, and Ubered to the airport in time to go through security and make our flight!

This spontaneous trip to Boston and our road trip all the way to Bar Harbor ended up being even more incredible than we had imagined. I'm so happy I was able to visit New England in the fall, and can't wait to go again!!

I hope this detailed guide of our complete road trip through New England in the fall inspires your next adventure. If you have any questions or want more recommendations, message us on Instagram @wildjoyexperiences!!

- The Wildjoy Team