Two Weeks Exploring New England and Eastern Canada

To quote “The Pirates Who Don’t Do Anything” from VeggieTales “I’ve never been to Boston in the fall!” This was our reality too, until this last fall (2022) when we took two weeks and visited the New England states and some of Eastern Canada. We saw the majority of New England by renting a car and driving, enjoying the beautiful fall foliage! We did about five days driving through Connecticut, Rhode Island, New Hampshire, Vermont, and Massachusetts, then a week-long cruise in the middle from Boston, MA, to Maine, St. John’s New Brunswick, and Sydney Nova Scotia, and then ended with a couple of days in Boston at the end. What an adventure New England and Eastern Canada were – we had a range of activities, food, and amazing fall colors!

New England

A brief overview of our New England driving tour: we started in Connecticut stayed overnight and drove through Rhode Island to Massachusetts where we stayed the night. Drove the next morning to New Hampshire, and the following day we visited Vermont and took two days exploring. Back in New Hampshire for a day visiting some friends. The next day back to Boston, MA to board our cruise ship. Cruise ports: Bar Harbor, Maine, Portland, Maine, St. John, New Brunswick Canada, and Sydney, Nova Scotia. After debarking from our cruise, we spent a couple of days in Boston, MA before heading off on the next adventure overseas. 


Frank Pepe Pizzeria Napoletana

When in Connecticut, we encourage you to stop in New Haven at Frank Pepe for pizza! This was our first stop/meal in Connecticut and it did not disappoint. New Haven is the location of the original Frank Pepe Pizzeria Napoletana which was established in 1925. It is still a family-owned business today and has added a handful of other locations. They use coal-fired ovens to cook the pizza which provides a delicious crispy and slightly charred crust. We tried the Margherita which consists of crushed Italian tomatoes, fresh mozzarella, fresh basil, grated Pecornio Romano, and olive oil. Pretty standard Margherita pizza, but it tasted wonderful with the fresh ingredients!

Mystic Seaport Museum

The Mystic Seaport Museum in Mystic is well worth a visit. It is like a small village with buildings that have various exhibits to tour. A few exhibits we saw were sailor artwork, ship mastheads, a small lighthouse, metalworking, and even a few ships in the harbors. There was also a restoration section and we saw employees who were working on various restoration projects with different ships. There is also a kids’ area with coloring and games. Our favorite part was walking through a couple of the ships in the harbor, we were amazed at how many shipmates would fit in some of these boats with such limited space! 

Rhode Island

Cliff Walk

We made a quick stop in Rhode Island on our way to Boston, MA, and were limited on time. We looked at a few of the New Port Mansions from the outside (we didn’t have time to go in and tour them, so we are hoping to make it back to RI soon and go through and see them). We did enjoy the Cliff Walk which was along the cliff line with the water on one side and many of the mansion estates on the other side. This was a great opportunity to take a break from driving, get some fresh air, and get a glimpse of Rhode Island. 

New Hampshire

Gould Hill Farm

Our first stop in New Hampshire was Gould Hill Farm – an adorable family farm. They have a store, bakery, and beautiful orchards. We were there for part of the apple season and so we purchased a peck of apples (you buy the size of the bag and then go to the orchards and fill it up). Depending on when you are there the apples that you can pick may vary as they are not all ready at the same time of the season. They explained which apple varieties were ready to be picked and there were signs in the orchard as well that told us which rows we could pick from. 

We picked some Honey Crisp, McIntosh, Macoun, and Cortland apples and filled our bag (a peck ended up being a lot of apples for just the two of us, we ended with 22 apples). All the apples were amazing and we enjoyed snacking on them over the next few days. We also went back into the store and got some of their homemade apple cider and a pumpkin whoopie pie (both were delicious)! 

The Mount Washington Cog Railway

We headed to the White Mountains for a ride on the Cog Railroad. It was a little rainy at the base, but the fall colors were so vibrant. Our guide, Terry, was wonderful. He made the tour fun and engaging and had great information to share. The average grade going up to the summit is 25%, and at its steepest, it is 37.4% – the benches in the railcar are at quite an angle to accommodate the steep grades of the mountain, pretty cool! There was one point where Terry had a few of us stand in the aisle of the railcar to show us just how steep the grade is – in the aisle, we were standing perpendicular to the flat ground which is at a severe angle to the railcar and so we ended up leaning forward quite a ways and were able to stay balanced. We love having interactive experiences on tours! 

As we went up the mountain the tree line thins out and the rain and wind picked up and the temperatures dropped. By the time the train reached the summit, it was around 20 degrees F with wind chill and 38 mph wind and rain. Our guide told us that the weather can change at any point to any kind of weather; Mount Washington is well known for having the world’s worst weather. We were told that the strongest wind ever recorded from Mount Washington was 231 mph (which makes our 38 mph seem like small potatoes). 

We would highly recommend a ride on the Cog Railway, book your tickets in advance as the seating and availability are limited. 

Omni Mount Washington Resort

Our guide, Terry, from the Cog Railway recommended a visit to this place while we were on our tour. It is not a long drive from the base station so we decided to go take a look. It is a beautiful estate! The resort looks like a castle, and the surrounding grounds are breathtaking. We walked through the lobby and out to the back balcony where the views of the mountains with the colors of the trees were well worth the visit. We did not stay the night but we did take a short walk on the grounds. 

Porfido’s Market & Deli

We were told that Littleton had some great restaurant options, but because of our detour to the Omni Mount Washington Resort, we drove through Littleton later in the evening and our options were more limited. We saw Porfido’s Market & Deli and went in to see if there were some simple groceries we could get for dinner. As part of their deli, they have some already prepared simple meals or you can order some hot food from the counter. They had a special that day for a Turkey Bomb sandwich that was the bomb! It was a relatively inexpensive meal that came with the sandwich and some fries and tasted great. 


Ben & Jerry’s Factory Tour

We took a tour of the Ben & Jerry’s Factory in Waterbury, VT. It is a concise and informational short tour (about 30 minutes). We listened to a brief history of the company, saw the production floor, tried some of their cookie dough chunks, and then at the end received a sample of strawberry cheesecake ice cream (we were told the sample flavors change and may vary on the day of your tour). After the tour, we took some pictures around the outside of the building and visited the Flavor Graveyard up the hill. The flavor graveyard is funny and contains headstones with the dates of all the flavors that have ever been released and when they were discontinued. Some flavors we noticed were retired, brought back, and retired again – but fun to see the many different flavors the company has produced since they started their first Scoop Shop in 1978! 

This is a tour that will need advanced booking – tickets are released on their website two weeks in advance of any chosen date.

Whistling Man Schooner Co. Sailing Tour

We bundled up in our jackets and coats and headed out for a brisk sailing tour on Lake Champlain with the Whistling Man Schooner Co. Captain Bubba and his first mate Eddy were wonderful guides out on the lake. They were very friendly, and personable, and had great information to share with us out on the water. They told some fun stories about the things we were seeing as well as other lake cruises they’d done.

Joseph Smith Birthplace Memorial

The Joseph Smith Birthplace Memorial is open year-round and is where the prophet, Joseph Smith, whom Jesus Christ restored His gospel through, was born. All are welcome to visit and take a guided tour of the visitors’ center and monument which is open year-round. You can drive or walk into the wooded areas to see the original foundations of homes that belonged to Solomon Mack and Daniel Mack. 


Red Sox Major League Baseball Game

We bought tickets the day before the game so they were pretty cheap. Driving in Boston and around the stadium was hectic, to say the least! Finding parking was a nightmare, but with some help from maps, we found a few different places and one of the few had available spots and a decent price for the time we were going to be parked there. The stadium atmosphere was so fun and the game was good too! If you enjoy baseball or just want to experience an MLB game – definitely look into tickets at Fenway Park. 

Freedom Trail Food Tour

We booked a Freedom Trail Food Tour in Boston and absolutely loved it! We had great food, and our guide, Guido, was fantastic! The food-tasting part of the tour came first and included some historical sights and lots of information. After the food tour portion, there were a couple of extra people who joined our group for a more extensive informational tour. Guido was entertaining in delivering the information throughout the entire tour! We enjoyed seeing the various historical sites, and the five food stops were excellent! 

Our food tour stops included: 

  1. Bricco Panetteria – amazing, fresh-baked bread.
  2. Caffe Vittoria – yummy hot chocolate and cannolis.
  3. Salumeria Italiano – fantastic Italian subs.
  4. Ernesto’s – pizza, was good but I’d say not the best pizza we’ve ever had, however, the crust was quite good.
  5. Beantown Pub – we don’t drink alcohol, so we ordered off the soda menu. Jeff tried the ginger beer and I tried the root beer. I think the ginger beer was better than the root beer which was a little too sweet for my taste.


We made a quick stop in Plymouth on our drive from New Port, RI on our way to the Red Sox games in Boston. We were here early evening and some things had already started closed for the night. But we did get to see Plymouth Rock and the outside of the replica of the Mayflower ship (it had already closed for the day). Plymouth Rock itself was smaller in person than I had expected it to be, and it is housed under a columned structure that also has an iron fence/rock wall around it the rock is on the ground inside there and has the year 1620 engraved in it. It was cool to see a couple of parts of the American History we learned about growing up in school in person. 

Foodie Finds

Just sharing a few foodie places that we enjoyed while in Boston.

  1. Finagle a Bagel – a wide variety of bagels, cream cheese, and bagel sandwiches (the smokehouse club was excellent).
  2. Luke’s Lobster – we tried Luke’s Trio which is a 2 oz lobster roll, a 2 oz crab roll, and a 2 oz shrimp roll. The rolls were small and it is a little expensive but they were delicious. 
  3. Omni Parker House – where the Boston Cream Pie dessert was first created, we got a small one and it was really good. 
  4. Quincy Market – a fun atmosphere with lots of different food options inside! We tried a place with taco salad and another place that served clam chowda and lobster bisque.  

Visiting Friends, Golf, and Roller Coasters

We spent a day with some friends of ours who live in New Hampshire and drove to the Crestview Country Club in Massachusetts for a round of golf and then to Six Flags New England in the evening for some roller coaster fun! It was great to catch up and spend some quality time with friends we have not seen in a while. And if you are looking for atypical tourist activities to do, a round of golf and/or enjoying time at a local amusement park are sure ways to have a good time and mix things up!


We took a cruise out of Boston, MA that had two ports in Maine, Bar Harbor, and Portland. So we only had the port time in each of these places, but here are some things we did and saw with our time. 

Bar Harbor Port – Acadia Gem EV Rentals

When we were planning our port days for the cruise, we happened upon the Acadia GEM EV Rentals. We looked at their website and what they offered and decided to book an electric vehicle with them that we could then take and drive around the Park Loop in Acadia National Park. The scenery was absolutely beautiful, we loved driving the Park Loop and enjoying nature. The electric vehicle is awesome – we only had a two-seater so finding parking along the side was pretty easy cause we could fit in much smaller spaces! We would highly recommend booking with Acadia GEM EV Rentals, it is a fun and unique way to sightsee in Acadia National Park. Book your rental early though, when we showed up there were a handful of people who wanted to book for that day but there were no vehicles available (unless someone did not show up for their reservation or returned their vehicle early and did not use their full rental time). 

The car only goes up to 35 miles per hour and is only supposed to stay on the places they tell you and show you on the map. Definitely stick to the map trail, we accidentally missed one of the turns and had to turn around, and going back up the hill we went down was a struggle! We had the vehicle on full throttle and were chugging up at 5 miles per hour, we felt terrible especially because we started having a huge line of cars piling up behind us that couldn’t pass on the turns. Once we got to a flat spot we pulled over so that all the cars we stopped could pass us safely, and we made our way back to the correct turnoff and didn’t have any other issues. 

We stopped and took a walk on one of the beaches and pulled over a few times to enjoy the views and scenery. There are some hiking trails as well along the route, we decided to take a more relaxed day and drive/walk around rather than a couple of hours of hiking. But we would love to go back to Acadia someday and try some of the hiking trails next time. 

The Highroller Lobster Co. in Portland

We did not have any shore excursions booked for Portland, so when we got off the ship we just walked around. We thought Portland itself felt more like an industrial city, so there was not a lot to do in and around Portland that we found. We did have a friend recommend to us The Highroller Lobster Co. to eat, so we did go there for some lunch. The Highroller Lobster Co. was fabulous! We tried the lobby pop (which is basically a lobster tail corn dog) and the surf and turf burger. It is a little more expensive as it is a lobster joint, but the food tasted amazing, we would go back and eat there again. 

Eastern Canada

Along with our two ports in Maine, we had two ports in Eastern Canada – St. John, New Brunswick, and Sydney, Nova Scotia. 

St. John, New Brunswick Canada

St. John City Market

Our first stop off the ship in Canada was the St. John City Market. There were dozens of local vendors there with different foods and wares. We love to collect artwork from the various places we travel and bought a beautifully painted print from a local artist that showcased some beautiful fall colors. We also bought a stunning hand-blown glass ornament from a different vendor. We were thrilled with our experience at the city market.

Rockwood Park

We walked from the city market to Rockwood Park (roughly a 30-minute walk), there is public transportation but we had a hard time figuring it out and decided to just walk. Rockwood Park is pretty big, so we visited the Inside Out Nature Centre and rented a couple of bikes so we could ride around. We loved Inside Out Nature Centre, the lady who helped us was incredibly friendly and kind, and she gave us a map and some suggestions of trails to ride and things we could see. We rode past a couple of lakes that were incredible! The water reflections we saw of the surrounding landscapes were the best we have ever seen, just breathtaking! The trails were really fun to ride and we ended up doing 8-10 miles which also gave us a great opportunity to get cardio in for the day. 

Tim Horton’s

Tim Horton’s is basically the Canadian version of Starbucks. We do not drink coffee, but we do like their hot chocolate, juices, donuts, and our favorites the Tim Bits (which are just donut holes). So if you are looking for a quick and easy place to get some donuts and a drink there are multiple locations of Tim Horton’s all over Canada!

Sydney, Nova Scotia

We stopped at the World’s Largest Fiddle and took a short walk around the town before getting back on the ship. We did not have a shore excursion planned for Sydney and the weather ended up being rainy and windy so we did not spend much time off the ship in Sydney. 

World’s Largest Fiddle

This was the most notable thing we saw in Sydney. We did not have to go far (or even off the ship) to see the World’s Largest Fiddle, it is located right at the cruise terminal! This fiddle and the bow stand at about 60 ft. tall. It was constructed in 2005 by Cyril Hearn and is a tribute to the folk music and traditions of the Celtic community of the province. 

Final Thoughts

We would highly recommend taking some time to tour New England and find some places in Canada to explore! We would love to get back up to Canada and see Prince Edward Island. The New England states are packed with history and a variety of experiences! We loved seeing the beautiful fall colors as we drove from state to state. We hope you found some new things or places to add to your bucket list!