Indian Summer: How To Enjoy New England And Eastern Canada #travel #roadtrip #indiansummer #newengland #canada #thingstodo

Indian Summer: How To Enjoy New England And Eastern Canada

Indian Summer

Summer is coming to an end slowly. The days become shorter, the temperature lowers, and the colors turn vibrant yellows, oranges, and reds. Soon, the fall foliage will be at its prime, and you will be stunned by so many colors—Indian Summer at its best! And the perfect opportunity to discover the New England States and Eastern Canada. Make up your fall travel plans and prepare for an Indian Summer road trip!

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Why an Indian Summer road trip through New England and Eastern Canada?

New England has a lot to offer, like stunning views, charming covered bridges, and you will never get tired of driving around because of the most picturesque trees you ever will see. Not to forget about spending Halloween in Salem, Massachusetts, Pumpkins everywhere, the Maple Syrup, and the original New England Clam Chowder. To experience an Indian Summer was always on my bucket list

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Indian Summer: How To Enjoy New England and Eastern Canada

A bonus was to extend the road trip with a detour to Eastern Canada. When would I ever have the chance to come close to places like Nova Scotia, Prince Edward Island, or New Brunswick?

Long story short, this is an itinerary for a 23-days road trip to New England and Eastern Canada during the Indian Summer!

Places mapped by Wanderlog, a trip planner on iOS and Android


Part I: U.S.A. – Massachusetts, New Hampshire, Maine

Massachusetts – Day 1-5

Day one consists of landing in Boston and heading to Cape Ann to spend the first three nights there. The best place to sleep is the Atlantis Oceanfront Inn in Gloucester. A brilliant Inn with an ocean view from all rooms to watch one of the most beautiful sunrises.

Indian Summer: New England, Massachusetts, Gloucester, Atlantis Oceanfront Inn

Explore the Peninsula on the second day with Whale Watching in Gloucester, visit an abandoned granite quarry at Halibut Point State Park, and have a walking tour through Rockport with its colorful houses. And do not forget to eat the freshest Lobster aside from the one in Maine.

Tours and attractions for Boston, Salem, and more while saving up to 55% with the Go Boston Card:

Indian Summer: Go City Card Boston

On day three, make a day trip to Salem and learn everything about the history of the dark time of chasing witches. The town is crazy about witches year-round, but you cannot escape those witches on Halloween anymore.

Indian Summer: New England, Massachusetts, Rockport #travel #thingstodo #new england #indiansummer

The fourth day is a travel day again. Leave Cape Ann, and head to the White Mountains in New Hampshire. Nonetheless, on the route to New Hampshire, stop by in Lexington, MA. Experience the first shot of the American Revolution and hop on to the tour to Concord and learn everything about the history of the birthplace of American Liberty.

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New Hampshire – Day 5-7

As soon as you arrive in the White Mountain National Forest*, settle down for a couple of days and start to discover the area. Hike around the forest on the Appalachian Trail. Explore the Flume Gorge and the Franconia Notch. Then stop by at the Echo Lake, or let your car “climb” 1917 meters to the summit of Mount Washington. And last but not least, enjoy the fall foliage to the fullest by driving the Kancamagus Highway that crosses the White Mountain National Forest straight through its heart.

Indian Summer: New England, New Hampshire, White Mountain National Park, Mount Washington #travel #thingstodo #roadtrip #newengland #newhampshire #indiansummer Indian Summer: New England, New Hampshire, White Mountain National Park, Mount Washington #travel #thingstodo #roadtrip #newengland #newhampshire #indiansummer

When you leave New Hampshire, heading to the coast of Maine, visit the “Castle in the Clouds” in Moultonborough, NH, overlooking Lake Winnipesaukee.

Maine – Day 8 -9

Begin day 8 with a bit of lighthouse tour. Start at the “Two Lights” at Cape Elizabeth, and visit the most photographed lighthouse ever, the Pemaquid Point Light, and run like Forest Gump as he finished his coast to coast run through the U.S. at Marshall Point.

Download my little lighthouse guide to follow the route to Maine’s best lighthouses and expect rough cliffs and rocky coastlines. You will feel enchanted by this unique landscape.


Indian Summer: New England, Maine, Lighthouse, Travel Guide #travel #thingstodo #roadtrip #newengland #maine #lighthouse #indiansummer


Stop at Portland for the freshest and most delicious Lobster ever, or get yourself some “fuel” for the second part of the day at “The Holy Donut.” They are the best donuts I have ever eaten. Caramel-Bacon is my absolute favorite!

Then stay the night at Bar Harbour and take it as the starting point of your day at the Acadia National Park. The 27-mile Park Loop Road connects all the lakes, mountains, and seashore of Acadia, like Cadillac Mountain, the Thunder Hole, or Jordan Pond, to name just a few highlights.

Before leaving Maine and the U.S. and entering Canada for the next stage of this trip, visit one more and my favorite lighthouse; West Quoddy Head Light. The tower with its distinct red and white stripes is just too lovely to miss that out.

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Part II: Canada – Nova Scotia, P.E.I., New Brunswick, Quebec, Montreal

Welcome to Canada! You can cross borders at Calais, Maine, and Saint Stephen, New Brunswick. I chose to stay overnight in an AirBnB in Saint Stephen as it was already late and dark.

Nova Scotia – Day 10-13

The plan for the next day was to drive to Halifax in Nova Scotia. So it was supposed to be a long journey.

Give yourself a break at Saint John, one of the bigger cities in this province. By chance, watch one of the highest tides in the world at the Bay of Fundy. Approximately 160 billion tonnes of seawater flow in and out here twice each day. In the late afternoon, it is time to settle in Halifax. If you still have some energy left, experience the nightlife of the capital of the province of Nova Scotia. Give yourself at least two nights here. It will give you the chance to discover some of the city’s best sights without worrying about driving to your next destination.

Travel to Peggy’s Cove and up to Cape Breton on day 12 and explore the Cape Breton Highlands National Park on day 13 before you leave Novia Scotia for the next Canadian Province.

Indian Summer: Canada, Nova Scotia, Peggy´s Cove #travel #canada #novascotia #thingstodo #peggyscove

Bonus trip to New Foundland

If you have one more week or are brave enough to change your plans, this would be the perfect opportunity to set over to New Foundland with the ferry. I did think about taking the boat and skipping all the rest of my planned route. But in the end, I decided to stick with it, and after all, I was happy that I did. Otherwise, I would not have met one of the loveliest guys in the world at the next destination.

P.E.I. – Day 14-15

P.E.I. is the abbreviation of Prince Edward Island. The first highlight is already beginning or better while you enter the island. The 13 km-long “Confederation Bridge” connects the island with the continent was mentioned in the National Geographic’s book “400 Road Trips, you will never forget!.

Charlottetown, the capital of the province of Prince Edward Island, is probably the best location to stay and explore the entire island. Start here and head to Point Prim Lighthouse to kick-off day 15.

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Afterward, make sure to visit Hannah’s Bottle Village. It was a coincidence that I stopped by. I had already passed it when I saw the road sign in my driving mirror. Fighting with myself, if I should leave it or not, I could not stand it and turn around. I just had to find out what it is as I am too curious. That was indeed one of the best decisions I made. This tiny village is hidden in the backyard of Gar Gillis house at Point Prim. It has everything you need for a proper town; a school, a hospital, a church, even a Christmas tree.

He built the tiny houses entirely out of empty glass bottles donated by his neighbors and the nearby chowder house. Gar Gillis is one of the loveliest people I have ever met. He showed me around when I visited the bottle village and told me everything about it. The entrance is free but if you like it, leave your change there as he donates all the money to the I.W.K. Health Centre in Halifax.

Indian Summer: Prince Edward Island, Point Prim, Hannahs Bottle Village Indian Summer: Prince Edward Island, Point Prim, Hannahs Bottle Village

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Hanna’s bottle village is one of the hidden treasures of P.E.I. but not the only highlight. Visit the Red Sand Cliffs, make an Anne of Green Gable’s Tour, explore P.E.I. National Park, Charlottetown, is waiting in the evening with its vibrant nightlife, pubs, and restaurants.

New Brunswick – Day 16

Day 16, the half of your trip is already over, but there are still plenty of things to come. Although this day is full of driving from P.E.I. to Edmundston, it is also full of incredible experiences. Explore living history at Kings Landing near Fredericton and watch fall’s red and golden colors alongside the St. John’s River Valley.

Indian Summer: Canada, New Brunswick, St. John River Valley

Quebec – Day 17

Day 17 leads you to Quebec City. Stroll Old Quebec, North America’s oldest streets. Take a picture of the world-famous Château Frontenac, the most photographed hotel on the planet, and wander the Quebec Citadel. Last but not least, cross the St. Lawrence River by ferry and have a spectacular view of Old Quebec.

Montreal – Day 18

The next and also the last Canadian destination is Montreal. You can stay here for one or two nights if you have enough time, as there is so much to see. Three hours of sightseeing tours with the hop-on-hop-off bus was enough for me. The starting point of the tour is a parking garage where you can leave your car for the following hours. So park it there and relax while seeing Montreal’s best sights. That is the first part of day 18. The second part will lead you back to the United States. Crossing borders one more time.

Part III: U.S.A. – Vermont, New York, Connecticut, Rhode Island, Massachusetts

This Indian summer tour’s final part begins with returning to the United States.

Vermont & Massachusetts – Day 18,5 -19

Back in the U.S., you will find yourself in Vermont. Visit Burlington for one of the best sunsets to conclude day 18.

Vermont is the state of the Maple Sirup. Unfortunately, fall is not Sirup season, but, at least, you can visit some Sirup farms and learn everything about the process itself and, of course, buy some Maple Sirup as a souvenir for your home.

After a Sirup tasting on the morning of the 19th day of your journey, it is time to head south, crossing Massachusetts. Visit Shelburne Falls and wonder and wander the Bridge of Flowers and watch the Glacial Potholes before you drive to your final destination in Newport, Rhode Island.

Rhode Island – Day 20 – 21

Settle in Newport for the rest of the trip and relax while exploring the city. Walk the Cliff Walk with fantastic views of the ocean. And don’t forget all the mansions, like the Vanderbilts or the Breakers.

Indian Summer: USA, New England, Rhode Island, Newport, the mansions

Furthermore, you can have fun while taking part in a Ghost walk and enjoy all the different fishes and sea fruits at the Newport Seafood Festival.

Massachusetts – Day 22 – 23

I headed back to Massachusetts, where this journey began. It is a 2.5 hours drive one way from Newport to Cape Cod. Therefore you can stay in Newport and combine it with a day trip to the Peninsula. With plenty of things to see and do like the beaches, the lighthouse, Provincetown, a beautiful little town, quite crowded, but still lovely, it is worth visiting. You will find the most delicious fried mussels in this area. For me, it was a long-lasting point on my bucket list. Do you have one more day left? Then you could go to Martha’s Vineyard.

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The beginning and the end at the same time; Boston! Depending on how much time you have you can easily spend two or more days here in the city.

At my East Coast-Christmas Tour a few years earlier, I already had the chance to stay here for two nights. On that day, I walked the freedom trail from the beginning at the Boston Common until the end at the Bunker Hill Monument. Unfortunately, I arrived a bit too late at the monument. The last entrance to the top was already through, and they did not let anyone in anymore.Indian Summer: USA, New England, Massachusetts, Boston, Bunker Hill Monument #travel #thingstodo

Because of that, I was more than happy that I still had half of the day until my return flight should depart. Guess what I did! Of course, I “accomplished” the final mission of walking the freedom trail. I went to the top of the Bunker Hill Monument!!!

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Indian Summer: How To Enjoy New England and Eastern Canada Indian Summer: How To Enjoy New England and Eastern Canada

Well, in the end, I was on time; it was a sunny and warm day in the middle of October. My birthday was only two days ago, and I spent it on the beach, as I wished. I did all the things I wanted to do on this trip. Happy and smiling, I drove to the airport and went back home. I love those kinds of trips. That is why I love traveling as you can do so many things to make yourself happy.

Enter Dream and Wanderland for new and exclusive posts and articles about New Hampshire, Massachusetts, or Eastern Canada. And do not forget to leave your thoughts in the comments. Have you experienced an Indian Summer yet? Which is your favorite New England State? I am curious about your comments!

29 thoughts on “Indian Summer: How To Enjoy New England And Eastern Canada”

  1. I grew up in New England, and this has so much information for a unique end-of-summer/early-fall trip through the whole area. I think I might have to add this to my travel plans for this year! Thank you for the inspiration!

  2. I can’t believe the scenery of this place – the ultimate place for a road trip! 🙂 wonderful writing too

  3. This would be such a fun route! I’d do it but I’d add Vermont to the list; it’s just as beautiful as New Hampshire and there’s a lot of great hikes, especially in Southern Vermont. Great post!

    1. Hi Krystianna, of course, Vermont is so beautiful. It the second last stop on this trip. I´ve been there before I headed to Rhode Island. So no worries, I haven´t forgotten it!

  4. What a lovely area — and the perfect time to visit! I’ve been to Conn. and Mass. in the fall, but I would love to drive this entire loop up into Canada and back.

  5. Wow what a fantastic post! Definitely going to check out visiting here now after reading this! what stunning photos too

  6. We’ve done a New England road trip a couple of years ago and it was amazing. Unfortunately we timed it a little wrong and missed the Indian summer by about two weeks… but since we only did a short trip and didn’t get to see even half of what we wanted to see, I’m sure we’ll be back for another. And your itinerary gives me a very good starting point for next time. Thank you

  7. I’m already upset that I missed out on doing something like this, this fall. It looks like a really beautiful trip. Thanks for the handy map!

  8. we have driven to maine (Belfast area) and back to NY, and MOntreal- NY on separate trips, you really got to do so much! I’d love to get up to Quebec city or the martimes in Canada. I believe you can do a ferry too from Maine to Nova Scotia!

    1. Harmony, there are indeed so many things to do in this area! I loved that trip! And it gave me some ideas on where to go again one day with more time then. Quebec is definitely worth a visit. It can be crowded, especially, the old town, but it´s very nice. I liked it more than Montreal.

  9. WOW! I wish I can also do the 23 days travel. All you photos are lovely, it makes me wanna visit those places. Especially, White Mountain National Forest, I love hiking and mountains, so this is perfect.

    1. Oh yes, Leigh, from New Jersey it´s not that far away and you can probably use your own car, which would save you a bunch of money. 😉

  10. Wow that is an epic road trip! I am planning on visiting New England next year so I’ll definitely be picking up on some of your tips.

  11. This looks like such a great trip! Hopefully I can go there someday. Great photos by the way 🙂

  12. Definitely the best season in that part of the world! As someone who used to live in Montreal, I really appreciate not only the beauty of this season, but also the weather (not as cold as in winter, and not as hot and humid as summers can be). I’ve also been to Boston which is such a nice city with really friendly people. Your itinerary sounds perfect if I ever make it back to that part of the world.

  13. Wow. That was a fun-filled and packed summer!!! I’ve never been to Canada or anywhere in ‘New England’, that’s why I’ve always wanted to go there. When the time comes, I will follow part of your itinerary! =)

    1. Thanks, Marysia that you stopped by! I´m glad that you like the post. I love this season of the year, too, and love to watch the leaves foliage! Those colors are magic! Do you have any plans for an foliage travel yet?

    1. Hi Brittany, that is awesome! I´m sure you will love that area! In the next few weeks, I will put more infos and details online. Do you already have an idea where you want to go?

    1. Oh yeah, Sheila, sooner or later you should visit! It is so amazing! What is it what you stop from getting over there?

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