New England Road Trip – 8 Days Of Discovery

New England, the North-East corner of the US, has always been a place that fascinated me. The six states that make New England (Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island, Vermont) not only have so much history in them, but also amazing nature, which gets even more amazing during the fall season. I have seen hundreds of autumn pictures from this area and I knew I had to see that beauty with my own eyes one day. It’s been almost five years that I live in New York, and I have yet to make the road trip in New England that I have been dreaming about.

In most of my recent travels, I preferred to fly out to remote destinations. Traveling far has felt more shiny and special. It led me to think that I am not the kind of person that goes out on the roads to explore parks and villages. Then Covid has arrived, and flying is not an option these days, so what could be better than doing something that was really “far” from me for so long?

Preparations for our New England road trip

In the past four years, I did two road trips, both with friends, in which I wasn’t the main organizer, nor the main driver. So, the preparations for this New England road trip felt like I was doing it for the first time.

I was excited to start planning, but also a bit stressed with all the information I was reading and saving. It’s that terrible fear of missing out that actually held me back from taking the first steps of building the plan. Once my partner was on board with the planning, we started connecting all the dots, and the excitement level has gone way up. The general plan turned into an initial itinerary and we could start dealing with the logistics – renting a car, finding a house sitter for our dog, etc.

If you want to read more about the planning, guidelines, and tips that helped us to prepare for and execute this trip, check out my 10 Tips For Planning For The Best Road Trip.

We put together all the information we have collected, together with our road trip guidelines, and we were ready to hit the road. The beautiful itinerary turned into a wonderful trip, which I share here.

Let’s explore my New England road trip!

Day 1 – Discovering the nature of Connecticut

After asking all the relevant questions at the rent-a-car company, we finally loaded the car with all our stuff and hit the road. We are on our way! The moment we left New York was when I felt that our road trip to New England has really started.

First stop – Squantz Pond State Park

The first destination was planned to be a lunch break at one of the lakes of Litchfield Hills in Connecticut. We made a short stop at the Connecticut Welcome Center, right before Danbury, and the nice rep helped us to figure out how to continue from here.

30 minutes drive up north led us to Squantz Pond State Park, where we sat down on a one single wooden bench, facing the beautiful pond, and having our lunch. This was only the first stop, and we were already amazed by the views. The pond was wide, with green hills showing first signs of autumn, surrounding it. The water was clean and it was all very quiet. There was no one else around us, even though there were a few more cars in the parking lot. We had all this view to ourselves!

We absorbed this calmness as much as we could until we were fully energized to move on.

Second stop – Kent falls State Park

Another 30 minutes drive up north led us to the beautiful Kent Falls State Park. There were only a few people around us, but it’s easy to see that in high-season or no-Covid19-days this place can accommodate hundreds of people.

The three lower falls can be seen from the parking lot, and a five minutes walk will get you there. I imagined what it’s like to be here on a hot summer day when you can get your legs wet in the cold water. We enjoyed this relaxing moment of gazing at the beautiful water and trees, and we then started climbing up to the top of the waterfall.

The crest is 250 feet up in the woods. Small balconies are facing the waterfalls on the way, in case you want to make a stop. The trees around us were greenish, and a golden carpet of autumn leaves covered the path. I felt like I was in a scene from a fairytale. We reached the top quickly and took some great pictures of the highest fall. There was no wide view from above towards the other waterfalls below us, but we still enjoyed it.

We went down back to the car and drove to Springfield, MA for the night. Our room was at Naomi’s Inn Bed and Breakfast. It is a house with rooms to rent on the first and second floors and the third is where the owner lives. The walls in the hallway had choc painting of Wizard of oz, and around the big piano, they had Alice in wonderland images and quotes. Breakfast was served contactless to the room. The place has a high rank on Booking, but we were not big fans (mostly for not being the cleanest).

Day 2 – All the way to Portland, Maine

After a light breakfast at the B&B, the rest of this morning was dedicated to shopping at Walmart. This was part of our plan for the first day, but we were flexible to move it to the second. We filled the car with water, snacks, and other foods for the road, and we started our drive towards Portland, Maine.

Portland Head Light

It took about three hours to make it to our first stop at Cape Elizabeth, just under Portland. We parked the car at Fort Williams Park and went to see the famous Portland Head Light. A trip to Maine must include at least one lighthouse! While the Museum and shop were closed due to Covid19, looking at the lighthouse from the outside is marvelous on its own. Walking around it, next to it, or looking at it from a distance, is like looking at professionally-taken photos. We started walking along the coastline of Fort Williams Park. We sat on one of the benches, enjoyed the sound of the waves breaking on the rocky shore, and absorbed the peace.

The city of Portland

We left Fort Williams Park right in time for an early dinner, so we headed to Downtown Portland for a pizza. Portland Pie Co. has a built-your-own-pizza menu with vegan crust, cheese, and toppings. It was perfect for us! It was one of the best pizzas I had lately. After we filled our stomachs we were ready to explore the city, however, the city had different plans for us. Most of the stores in downtown Portland were already closed, but it didn’t prevent us from feeling the good vibes of this place. It was unfortunate we couldn’t get more of it.

The next stop was the Eastern Promenade of Portland. It was already getting dark, but there were still many people strolling in the park with their dogs, laying on the grass or sitting on the benches, gazing at the gorgeous Casco Bay and its islands. We joined the strollers for a short while until it really got dark. It was time to leave the city to our hotel Hampton Inn Portland-Airport in South Portland. The room was huge, they had a nice outside seating on the lobby floor and the staff was kind. Spoiler alert – we liked it here so we returned later on in this trip.

Day 3 – Bar Harbor, here we come!

After two days of perfect weather, we woke up to a gray sky with a forecast of rain most of the day ahead of us. Rain on a road trip might ruin some of the fun, but we are not letting anything stop us.

We started with a breakfast-to-go from The Sinful Kitchen. It’s a popular restaurant on the weekends, and we didn’t book a table in advance, so we had our breakfast in the car. Not the most convenient way, but still delicious. Happy and full, we were ready to start our third day of the trip.

After 15 minutes drive north on I295, the rain suddenly stopped. A look at the map showed us that we were close to Wolfe’s Neck Woods State Park, so we made a quick update to our route, and exited the highway towards it.

Wolfe’s Neck Woods State Park

Since it was a spontaneous decision, we didn’t know what to expect from this park. We crossed the town Freeport and drove a few more minutes into the park. There were other cars in the parking lot, and we even saw one family having a picnic with their little kids running around. It warms the heart.

We started walking in the woods and the water of Casco Bay peeked out from behind the trees. The forest was amazing! The high trees covered the sky and were still green. On the trails, however, brown, yellow, and red leaves piled up, giving a perfect autumn vibe. We found a wooden staircase descending into the water, with a beautiful view of the bay and the islands. Then, in the middle of the woods, we sat on a bench, listening to the birds and squirrels. Oh yes, and take a few pictures. I was hoping to see other animals too, but we weren’t that lucky.

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Arriving to Bar Harbor

We left the park with a great feeling of satisfaction about our spontaneous decision. Not just that we saw this beautiful place, we also took great advantage of the no-rain.

On the way out, we wanted to stop on the main street of Freeport for a short walk and a coffee. Once we got our coffee, the rain came back, so we rushed back to the car and continued our long way towards Bar Harbor. This drive was probably the most boring one we had on this New England road trip. It was mostly on a highway and with the rain, we couldn’t enjoy the scenes around us (we barely saw anything).

We made a short lunch break at Ellsworth which is pretty close to Bar Harbor and I couldn’t wait to get there already. 30 minutes after, we entered our hotel, Bluenose Inn, at Bar Harbor. This is the only hotel we booked in advance and I looked forward to our stay here for two main reasons. First, this is our base for going to Acadia National Park, our Anchor destination, and one of the best national parks in the USA. Read more about the anchor destination in 10 Tips For Planning For The Best Road Trip. Second, I wanted to dip my body in their hot swimming pool!

Bar Harbor – we made it!

We checked it, unloaded all the bags from the car, and made the last preparation for the next day at the park. Once done, we immediately changed into our bathing suits, put bathrobes on, and made our way to the hot pool. It was great to discover they also had a hot tub. These 20 minutes in the bubbly water were exactly what we needed! So relaxing!

The time for Friday dinner has arrived and we headed to Downtown Bar Harbor. We had good Asian food at Siam Orchid, which was very vegan friendly and delicious. Most of the stores in the city were already closed when we finished our dinner, and it was unfortunate. We were really impressed with this town after only a short walk and we hoped to have more time to spend here later.

Preparation for Acadia National Park

Initially, we planned to use the park’s visitor center the next morning for detailed information about the hikes, but the hotel staff was super knowledgeable and helpful, and they gave us most of the information we needed. It’s so good to just ask.

On Recreation.gov we bought our site pass ($30 per vehicle, valid for 7 days). Two main roads of the park required additional unique passes – Sand Beach Entrance and Cadillac Summit Road. These passes were $2 each, and an entry time was to be selected (with a 30 minutes window). The additional two passes were only required between Oct 1 to 18 2020 as a pilot for the park’s new vehicle reservation system, so it’s better to check in advance if they or similar are still required during your trip.

This is the plan we made:

• Morning – enter Sandy beach, and take the Beehive trail.
• Afternoon – a short rest and go up to the Cadillac summit road for a view of the surrounding area (close to sunset).

Day 4 – Acadia National Park

The morning we waited for, has finally arrived. We got out of bad easily, knowing that we have a long day ahead of us at the park. Bagels with PB&J were our breakfast and we prepared two more to-go for an energy break during the hike. We also had vegetables and snacks in our backpacks and the car, so we were all set in terms of food and energy boosts.

First, we stopped at the Hulls Cove Visitor Center, only 3 minutes drive from the hotel. We still wanted to make a final consultation about our plan, and we knew it was going to be a quick one. I am so happy we did that, as they recommended us to add two more trails to our planned trek, and still within the time we had. Lucky us – we can experience more of the park!

Sand Beach and the Beehive trail

We drove about 20 minutes from the visitor center to Sand Beach on the Park Loop Road. Our entrance pass was for 11 am and we made it there on time. With a little patience, we found a parking place inside the parking lot (while others parked on the road’s sideways) and we went down to the beach. This is the only beach with sand in the park, and it is really a beautiful one. It’s not big, but it is nestled between low mountains and rocky shores. With the sun warming us up, it was the perfect spot to start our day.

Across the road from the parking lot is the entrance to the Beehive trail. After 0.2 miles through the trees, we reached an intersection and needed to choose between the easy route (the Bowl trail) and the hard route, which includes vertical climbing on iron bars up to the 450 ft. cliff. We were ready for the adventure so we chose the hard route, which apparently wasn’t that hard after all. It does involve climbing on metal ladders and walking on exposed edges, but nothing that we considered as hard. The people around us on this trek included younger kids and couples in their 50s-60s, and they all did it.

As the trail ascends, you see gorgeous views of the park’s coastline, including Sand Beach. The sight of the wide ocean on one side and the autumn trees on the other side is really breathtaking. There are many points to stop, enjoy the view, and take pictures. Once we reached the summit we sat down for a longer rest, breathing in all this beauty around us.

The Bowl and the Gorham Mountain trails

From the summit, the trail continues and descends to the bowl, which is a beautiful pond surrounded by mountains covered with autumn colored trees. so peaceful! The Bowl trail goes along the south side of the pond for about 0.4 miles, and then we turned left into the woods.

We continued to walk on the Bowl Trail until we reached the next intersection. Instead of staying on this trail that leads back to the parking lot, we chose to turn right and started a new trail – Gorham Mountain. This is a 1.4-mile, much easier trail. The first part goes on the rocky mountain, with views of both the other mountains of the park and the coastline. On the summit, we stopped to fuel ourselves with the PB&J bagels, and we continued down as the trail descends through the woods and on big granite rocks.

The end of the trail is on the Park-Loop Road. From there we went on the Ocean Path trail back to the parking lot of Sand Beach. This trail goes alongside the road on one side, and with red cliffs that fall into the water on the other side. There are many spots, including the main Thunder Hole, to step off the trail and to see the ocean waves crashing into the red rocks. It makes you feel how powerful the ocean can be.

Cadillac Mountain

We made it back to the car and were happy to sit down and let our legs rest. Our entrance pass to the Cadillac Mountain Road was for 4 pm and we had an hour to refresh ourselves and get there (including 30 minutes drive).

Cadillac Mountain is the highest peak in Acadia National Park and the North Atlantic seaboard, with a summit at 1530 feet (466m). Between October and March, this is the first point in the United States to see the Sunrise. We arrived in the late afternoon, before sunset, and we could see a 360 degrees view of the area. The bay, the islands in it, and the other mountains of Mount Desert Island. It is not the highest peak I have been to, but the amazing view made me feel like I am at the top of the world. I guess it’s all relative after all.

Downtown Bar Harbor

We still had a couple of hours of light, so we decided to drive back to downtown Bar Harbor and check out the streets when everything is supposed to be still open. To our surprise (after yesterday), the town was now full of people! It was a Saturday evening after all. There were lines and long waiting times in most restaurants, but we found a table, probably the last one available, at McKay’s Public House. They had limited vegan options, but a burger (the Impossible) with fries and Brussel sprouts as a starter, was exactly what we wanted.

Then, we strolled on the town’s streets, going between the stores and enjoying the festivity around us. We even found CJ’s Big Dipper that sells non-dairy ice cream (soy/almond milk-based) for a dessert. We bought some souvenirs – this is defiantly a place to remember – and headed back to our hotel. Tired after a long day but very satisfied.

Day 5 – The towns of Maine

After Acadia National Park, the next anchor destination of our New England road trip was Boston, which is five hours south of Bar Harbor. The plan for this day was to get ourselves closer as much as possible, but still make it interesting. Instead of driving on the same road I95 that we came on, we took state road 1 down south. This road winds along the coastline of Maine and passes through lovely small towns like Searsport, Belfast, and others. Our stop was planned to be at Camden.

Once again the rain wasn’t in our favor and it was pretty cold in Camden. We found a warmer place to sit in and have a yummy pizza for lunch at Blaze. We sat on the bar in their covered and heated terrace and had a great view of the Marina. Luckily the rain stopped and the sun came out (still cold though), so we could walk in the marina and on Main street. From the Harbor Park, we had a gorgeous wide view of the Marina under the cloudy sky. Camden is a really cute town and it was clear why people come here for weekend vacations.

From Camden, we continued our way down south to Portland. The room we booked for the night was at the same Hampton Inn Portland-Airport. It was great last time, the distance and location were convenient for us, and it was an easy decision. The hotel is located in front of The Maine Mall, so that night included a little bit of shopping as well.

Day 6 – Boston, the biggest city in New England

We were 90 minutes away from Downtown Boston, so we drove straight to the big city, without spending time on the way. I have been to Boston once for work in 2018, but it was such a short and busy trip, that I didn’t have any idea how the city even looks like. As excited I was to visit Boston again, so was my disappointment with the first impressions of this city.

From a tough beginning to a great day

Let me explain.

First, the massive road system at the entrance of the city, including bridges and tunnels, is super impressive. However, for first-time visitors, it was a disaster to find our way into downtown Boston. The GPS doesn’t work inside the long tunnels and we kept missing the right exits. I was going in circles until, by a fortunate mistake, I took another wrong exit that finally led me off the highway and into the city’s streets.

Then, we needed to look for a place to park and start exploring the city. The famous Freedom Trail appears on Google Maps as a dot, that turned out to be just a random place. Parking in the nearby streets was only for residents, and parking in a garage was more than $20/hour. Big city life. With not much of a choice, we parked the car close to the dot that Google Maps took us to.

We were finally able to locate where we were and where we want to go to. From here, everything just got better.

Exploring downtown Boston

Boston’s landmarks are located along a 2.5-mile red-brick trail, called The Freedom Trail. All these sites, from the Boston Common to USS Constitution, are related to the American Revolution. After the time we spent in finding our way, we had less time than we initially planned, so we followed the trail only from Old North Church to the Old State House. Most of the sites were closed due to Covid restrictions, anyway, and others open only on weekends.

In our stroll, we also passed by Quincy Market in Faneuil Hall Marketplace. This is an indoor/outdoor marketplace with food stands and some arts and crafts sellers. Also here, the Covid situation had its impacts and it was only partially open. We grabbed a falafel for a quick lunch and appreciated the quiet around us, however, I really hoped that soon things will be much better for all the businesses that suffer great losses during this time.

The streets of downtown Boston have a very special charm. The architecture style is a very old English one with other European influences. The old buildings are surrounded by modern buildings and glass-covered skyscrapers. This combination creates a beautiful mosaic of old and new architectural styles. Walking in the streets of Boston is a pleasant experience and after a short while, I fell in love with this city.

Boston’s Newbury street

Our next stop in Boston was Newbury street in the Back Bay area of Boston. On one side, this is a one-mile-long street with hundreds of shops and restaurants. On the other side, it’s like walking in a living museum of 19th-century architecture. The brownstones on both sides of the streets are uniquely amazing, and when you cross over to the next streets you see more of this old and beautiful style of Boston. I was really impressed! Did I mention that I fell in love with Boston?

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After we explored Newbury and the surrounding streets, we went to get dinner at Landwer Cafe (900 Beacon street). They have a good variety of vegan dishes, and their Rosalach for dessert tasted heavenly.

We were now ready to leave Boston. We started our drive towards Taunton, Massachusetts, to the Holiday Inn Taunton-Foxboro Area. To avoid traffic, the GPS took us through the neighborhoods of Brookline and South Boston. The drive on these small roads, through fancy neighborhoods with luxury houses, green parks, and ponds, was an unexpected and lovely surprise.

Day 7 – Cape Cod and Provincetown

When you type Cape Cod in Google Maps, it leads to a place in the middle of the peninsula, where there’s a big shopping mall. Located one hour drive from our hotel, we thought this could be a great place to stop for a coffee break, on our way further to Provincetown. And so we did. We arrived early so most of the stores haven’t opened yet, but we were able to get a coffee at Starbucks. It was inside the Barns and Nobles store, so I also got myself a new book. The bonus of the day.

Provincetown was one hour drive away from the mall, and we planned to stop also at the Cape Cod National Seashore on the way. The interesting thing about Cape Cod, at the time we were there, was that fall hasn’t started here yet. All the trees were still completely green and the views here were significantly different than what we have seen so far.

Cape Cod National Seashore

Our first stop was by the Cape Cod National Seashore Museum. We didn’t enter the museum but we walked around the pond behind it, enjoyed the sun, and watched ducks flying above the water, searching for food.

The second stop was at the Marconi Wireless Station, where you can get with the car almost to the beach. This is the site of the first transatlantic wireless communication between the United States and Europe in 1903. The station was abandoned a few years later due to erosion from the ocean and moved to another location. However, standing here and looking at the wide blue ocean, It is crazy to think about how such a pretentious project was planned more than 100 years ago and actually succeeded.

We walked on the marked trails on the sandy hills by the beach. The ocean was dark blue, beautiful, and quiet. The sandhills on the other side were spotted with green bushes, desert style. I looked towards the horizon and imagined the old and big sailing ships, bringing immigrants from Europe to the land of unlimited possibilities, approaching the shore.

I guess that the visit to Boston has left its mark on me.

Provincetown, Massachusetts

Originally we didn’t plan to drive all the way to Provincetown, but like most other choices we made during this New England road trip, I am happy we eventually did.

I heard it’s a gay-friendly town, but it was a surprise to see the pride flags everywhere. and I mean EVERYWHERE – on houses, guesthouses, restaurants, shops, and also in the gas station. Now, that’s the way to make us feel welcomed. We parked the car and started exploring the center of the town. It was the middle of the week so we didn’t expect to see many tourists, but there were. Even if not to the full capacity that this town can accommodate, it was still lively and happy. Some guesthouses even had their no-vacancy signs on.

We walked in the main street, entered souvenir shops and other lovely stores and we thought how fun this place can be for a summer vacation next year. We grabbed a quick lunch at Big Daddy’s Burrito (sat on their terrace and enjoyed the ocean view) before we went back to the car.

The last night of our New England road trip

At this point, we needed to book a hotel for the night, and we had Rhode Island in our way. Since it was a high-Covid state at the time of our trip, we needed to avoid staying in it. The options were staying either right before Rhode Island or right after Rhode Island. Eventually, we found La Quinta by Wyndham Norwich-Plainfield-Casino, at Plainfield, Connecticut, right after Rhode Island. A long drive is ahead of us, about three hours from Provincetown.

We stopped again at the Cape Cod Mall for a refresh-break and to get dinner to-go, so the three hours turned almost into four. It meant that I needed to drive at night. While around big cities the roads are well lit, most of the other roads we drove on were completely dark and narrow. The driving experience wasn’t fun, and I just wanted to arrive at the hotel. This was one of my guidelines for this trip, which this night I didn’t follow, and it proved to me why it was an important one. Eventually, we arrived at the hotel, exhausted but happy.

Day 8 – Connecticut and back home

This is the last day of our trip and a sad feeling started to fill me up. I really enjoyed everything we did (except for the drive last night), and didn’t want this to be over. But it was time to wake up from this dream and go back to reality. Not before we spend the day in Connecticut.

The first destination was planned to be New Haven. We left the hotel pretty early, and we didn’t have a long way ahead of us. We noticed another state park on our way, Rocky Neck State Park, and as we learned that being spontaneous is the best, we exited the highway towards it. The road led us to the parking lot, and we discovered the beach. It is one of the most beautiful beaches I have seen in the US. It wasn’t too wide or too long, but it had white sand with seagulls flying above us. The sun was in the middle of the sky, painting the water with shiny golden lines. To the east, we saw the fancy houses of Giants Neck, and to the west, behind the rocks, stands the Pavilion at Rocky Neck (an impressive event venue).

Just this morning in our car, we discussed how much we enjoyed this trip, but we don’t feel like we have rested enough. We thought about how we need to take another vacation after this vacation. And Voila, our luck has brought us to this charming beach, where we could get a little bit more of that relaxation, even if just for a short while.

New Haven

We chose New Haven to be our main stop for today because of the interesting historical landmarks, but not only. It was also for the vegetarian/vegan restaurant that we read good recommendations about – Claire’s Corner Copia. We had a delicious and interesting mid-week brunch which I highly recommended, and we then walked around New Haven Green.

The Green is a park in downtown New Haven that dates back to 1638. It was built by the Puritan colonists as an area dedicated to community and social life, recreation, and education. Interestingly, it is still used for the same purposes today. In the park, three old churches are standing for 300-400 years. Around the park, there are more colonial-style buildings like the visitor center, the public library, the new city hall, and others. The most impressive building is the old campus of Yale University. The architecture style and the big gate in the middle of the block reminded me of Harry Potter’s school – Hogwarts. I wonder if you’d think the same. Like in other places, the historical sights here were also closed, so we saw them from the outside and headed back to our car.

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New Haven wasn’t the last place we visited on our New England Road Trip. We made another quick stop in Bronxville, right before entering New York City, and it was a surprise to see how lovely (and rich?) this place is. So close to home, and I have not heard of it before. This place was like the cherry on the cream.

Final thoughts

That’s it, the trip was now over and we arrived back home.

Our New England Road Trip was much more than I expected it to be. I have been to so many new places and seen so many unexpected sights. We spent good hours in the car, talking, laughing, and listening to music. I learned so much and was happy to put on the Explorer hat again, after so long. I discovered new things about myself and allowed old parts of the young me to come out again. As different as it was, I was out of my comfort zone, and I loved it!

The only thing left at this point is to start planning the next trip. I have so many ideas for more road trips now, and just need to figure out how and when to execute them all.

If you reached this far, I thank you for reading and hope you enjoyed it. For updates about new posts from The Top Ten Traveler, subscribe to my newsletter below, and also get the ultimate packing list for free.

New England Road Trip – The hotels I stayed in

Day 1

Day 2 and 5

Day 3 and 4

Day 6

Day 7

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Tagged New England, North America, United States