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United States, New England, Newport, Provincetown, Cape Cod, Portland (Maine), Bar Harbor, Quebec, Montreal, New York State, Central Valley

2 weeks road trip through the East Coast and Canada

I'm traveling with a friend and it's our dream to visit New England and Canada. We love small towns instead of big cities. What do you think about this itinerary:
NY (2 days because we have been there twice), Newport (1 day), Provicentown - Cape Code (2 days), Portland - Coast of Main - Bar Harbour (4 days), Quebec (2 days), Montreal (2 days) and the last day we want to spend a complete day shopping so we are thinking going to Woodbury Common in Central Valley and then back to NY. Somewhere worth visiting between Montreal and Central Valley?. Our travel starts and finishes in NY and we would like to rent a car. We are not visiting Boston, because we have been there.
Any suggestions about the itinerary? We will be traveling on September or October. Which month do you think is better?
I have heard that October is beautiful because of the color of the trees.
Thanks a lot for your guidance!!!

20 Answers

top answer by
Nathan from Vermont

I agree with Melissa, that's a lot of driving. If you're OK with that then it looks like a good itinerary.

I recommend late September or October to catch the best foliage. Check this map out, click play to see the typical foliage schedule:

As for Maine, you can see much of Portland (Maine) in one day. Hit the West End, downtown/Old Port, and if you have another day take the ferry to Peaks Island. I recommend at least two days for Bar Harbor. It's beautiful, lots to do and hard to leave.

The real beauty in the Portland area is outside of Portland though.

Two must visits: Two Lights State Park. Bear right to the park when you arrive, not left toward the lighthouse. Park and head toward the water on the right. It's simply gorgeous. And Fort Williams Park, home of the most photographed lighthouse in the world!

And take a look at Freeport (Maine) when you're driving up the coast of Maine. L.L.Bean mothership store is there and it's a great shopping town.

Mentioned in this answer:

  1. Maine (state)
  2. Portland (Maine) (city)
  3. Bar Harbor (city)
  4. Two Lights State Park (attraction)
  5. Fort Williams Park (attraction)
  6. Freeport (Maine) (city)
  7. L.L.Bean (attraction)
  8. Peaks Island (island)
10 thankscomments (1)

answered by
Courtney from Los Angeles

I agree that that's a lot of time spent driving--I think your idea about cutting out Canada this time around is a good one! I also think you're going to love seeing that part of the country in the fall--it's absolutely gorgeous!!!

I think you might be giving yourself not quite enough time in  Newport. It's one of my favorite places in the world and a lot of the reason people go there is to see the giant mansions that were owned by a lot of the country's first real gazillionaire families. My favorite is the  Rosecliff. I don't remember who owned it but it's been featured in a million movies. I also love  The Breakers which I believe belonged to the Vanderbilts. They're all a little ostentatious but so much fun--I would think about maybe adding a day if these interest you. I would also see if the  Green Animals Topiary Garden is open when you go which is a lot of fun as well. 

My favorite place to stay in Newport is the  Marshall Slocum Inn I think I actually stayed there the first year it was open and many times since. It's a really lovely place and the people who run it are great. 

Personally, I would cut out Woodbury Common Premium Outlets--with so much beauty in the area it seems like such a shame to spend your time in stores you can visit just about anywhere else in the world, but I get it if that's what you want to do. :) 

Mentioned in this answer:

  1. Rosecliff (attraction)
  2. The Breakers (attraction)
  3. Woodbury Common Premium Outlets (attraction)
  4. Green Animals Topiary Garden (attraction)
  5. Marshall Slocum Inn (hotel)
  6. Newport (city)
6 thankscomments (2)

answered by
Annemarie from New York City

I'm not exactly sure of the direction, but not too far from Quebec you can visit Lake Placid, New York, the site of the 1980 winter olympics. There are a number of adorable bed and breakfasts, including my personal favorite Mirror Lake Inn Resort and Spa (some of the rooms have hot tubs and patios overlooking the lake!), and there are a few adorable restaurants and cafes in town. It's a sleepy village, but they love their sports and have a huge local complex, an ode to their olympic heritage, if you're into that kind of thing. 

I have never taken the trip in that direction myself, but every time I've been to Lake Placid, there have been hordes and hordes of Quebecois folks, so I know it's a destination for them and the distance isn't too great.

A few other towns on the New York State Throughway between Quebec and Woodbury Commons:

Kingston (New York): Definitely visit Historic Uptown Kingston and eat at vintage shop/cafe Outdated.

Woodstock (New York): About 30 minutes off the beaten path, but a cant-miss stop filled with independent theatres, shops full of tie-dye shirts, general stores with locally-made and sourced flannel shirts and two great restaurants, Cucina and Red Onion.

Newburgh: Another hip downtown with vintage shops and food trucks.

New Paltz: A doughtnut town with a college problem.

Milton: If you can swing it, stay the night at Buttermilk Falls and eat at their home restaurant -- they cook straight from the farm in their backyard.


Mentioned in this answer:

  1. Lake Placid (city)
  2. Kingston (New York) (city)
  3. Woodstock (New York) (city)
  4. Newburgh (city)
  5. New Paltz (city)
  6. Mirror Lake Inn Resort and Spa (hotel)
  7. Outdated (restaurant)
  8. Cucina (restaurant)
  9. Red Onion (restaurant)
  10. Milton (neighborhood)
  11. Buttermilk Falls (attraction)
6 thankscomments (2)

answered first by
Melissa from St. John's, Newfoundland

How many days do you have total? Keep in mind that it's about a 6 hour drive from Bar Harbor, ME to Quebec City, 2.5 from QC to Montreal and another 6 from Montreal back to NYC. If you don't count your travel days in your schedule above I think you'd be fine but if you only have 14 days total I'd reign it in and concentrate on a smaller area with less driving between stops.

Mentioned in this answer:

  1. Bar Harbor (city)
  2. Quebec City (city)
  3. Montreal (city)
6 thankscomments (2)

answered by
Alyssa from United States

One of my favorite restaurants in the Vieux Quebec area of Quebec City is Cochon Dingue (Le), especially for breakfast!  Very casual and not too expensive but delicious!

Mentioned in this answer:

  1. Vieux Quebec (attraction)
  2. Quebec City (city)
  3. Cochon Dingue (Le) (restaurant)
3 thanks

answered by
Joanne from Mississippi

Love your itinerary. Adding my two cents: how about taking the ferry over to Martha's Vineyard for an overnight stop. Beautiful island, charming B&Bs, can rent bicycles to tour, should be lovely color at that time. Need to make ferry reservation at Woods Hole.  And don't forget to have a traditional lobster roll while in Maine, while sitting on the beach or rocks overlooking the water. 

Mentioned in this answer:

  1. Martha's Vineyard (attraction)
  2. Woods Hole (city)
  3. Maine (state)
3 thanks

answered by
Rhiana from New Hampshire

Your day in Newport RI should is going to be great! The downtown area is perfect. There are shops everywhere and plenty of restaurants. For lunch, I would suggest the Black Pearl for a bowl of clam chowder(it is the absolute best), a little shopping for the afternoon, maybe some ice cream. If you want to see a beautiful sunset, I suggest the Hyatt Regency Newport on Goat Island. You don't stay there for the night, you go to the restaurant in the back and they have a sunset ceremony with champagne and a little canon every night. They have a fire pit, a little lighthouse, and the Newport Bridge is near. It will be warmer in September, but if you're looking for the leaves changing color I clearly suggest october. You will love to go and take the scenic route up through Franconia Notch where you'll pass the Presidential mountains, the spot where the Old Man Of The Mountain used to spend his days, and see all of the beautiful colors on the trees.

Mentioned in this answer:

  1. Black Pearl (restaurant)
  2. Franconia Notch (attraction)
  3. Old Man Of The Mountain (attraction)
  4. Hyatt Regency Newport (hotel)
  5. Goat Island (island)
  6. Newport Bridge (attraction)
3 thanks

answered by
Will from Chelsea (Massachusetts)

If it fits into your driving  schedule, I would suggest  Portsmouth (New Hampshire) and  Burlington (Vermont). Both are cute, small cities with great New England Charm. If you could do an overnight at either one or both, that would be great but they're also fun as a full or half-day stop.

There are a lot of great suggestions here. If possible, keep Quebec and Montreal in your itinerary. I've done road trips with friends of 3 days for both cities and it included driving back and forth from Boston. They're both so much fun, especially Quebec.

If I were to offer any suggestions, it would be to trim any trips that take you out of the nice loop you've created here. For example, can you do  Cape Cod without going all the way to  Provincetown or the coast of  Maine without going all the way to  Bar Harbor. I don't know, just a thought.

Personally, I'm an optimistic road tripper and feel that you can do it!

If you want to meet a fellow Trippy member while you're passing through Boston, let me know! I'd be happy to get a drink or do lunch!

Mentioned in this answer:

  1. Portsmouth (New Hampshire) (city)
  2. Burlington (Vermont) (city)
  3. Provincetown (city)
  4. Maine (state)
  5. Bar Harbor (city)
  6. Boston (city)
  7. Cape Cod (city)
3 thanks

answered by
Trang from Mont Tremblant

September October is a great time for Canada. It is not to cold and not to hot. I would recommended Quebec City gorgeous city where it is mostly walking. Park you're car, most of the city will be on foot.

Wow a lot of driving but the drive will be scenery. I would recommend if you are staying in Montreal is to stay in old Montreal. Very romantic. If you like to shop, go on Rue Sainte-Catherine!

I think thats pretty much all advice i can give you, hope this helps and i hope you enjoy your trip!


Mentioned in this answer:

  1. Quebec City (city)
  2. Rue Sainte-Catherine (attraction)
3 thanks

answered by
Missy from Newport

Hi, I agree, good idea to remove Canada from this great trip, and organize a trip just to Canada next time.  Personally, however it is my home town, so I may rate the town higher, but I think you should spend 2 days in NewportNewport has the largest number of buildings still standing from the Colonial Era, many open for tours, and a large number of "Summer Cottages", i.e. mansions from the Gilded Age, many of which are also open for tours.  Newport is the location of the oldest Jewish Synagogue, oldest state capital building still standing, longest continuously running tavern in the U.S. and has the 2nd largest deep water harbor on the eastern side of North America.  Add beaches, a busy harbor filled with luxury yachts, the Atlantic Ocean, and Ocean Drive, plus a very lively night life and there is plenty to see and do.  Here is a Youtube slideshow of Newport:  Glimpse of Newport, Rhode Island.  Beware of traffic delays to attempt to visit Provincetown by driving out and back in 2 days.  While driving mileage from Newport is around 120 miles, there is only one highway all of the way out to Provincetown, and summer traffic can be very heavy.  An alternative could be to visit Woods Hole, Hyannis, Hyannis Port, and Chatham (Massachusetts) for a feel of the Cape one day, and then take a day ferry out to Nantucket from Hyannis.  While in Portland (Maine), if you have time, take the ferry out to Monhegan Island, with a tiny little village and miles of hiking trails through woods that must be filled with fairies, given the many fairy houses found in the roots of trees.  Here is a Youtube video of photos I took of the fairy houses I saw while hiking:  Fairy Houses of Monhegan Island After Maine perhaps drive west to Burlington (Vermont), a very nice Vermont city on Lake Champlain.  There are micro breweries, chocolate factories, cheese makers, wineries, and of course Ben & Jerry's, along with boutique shopping, apple picking, and a lot of history.  Fall Foliage is usually more colorful inland than along the coast. After Burlington, you could drive south down surrounded by fall foliage, down the Hudson River, through Hyde Park (Vermont), Tarrytown and Sleepy Hollow, NY.  In the Hudson River Valley, there are wineries, museums, and several historic homes such as the Roosevelt Family Homes open for touring.  You could then end your trip right where you started in New York City. 

Mentioned in this answer:

  1. Newport (city)
  2. Provincetown (city)
  3. Woods Hole (city)
  4. Hyannis (city)
  5. Hyannis Port (attraction)
  6. Chatham (Massachusetts) (city)
  7. Nantucket (city)
  8. Portland (Maine) (city)
  9. Maine (state)
  10. Burlington (Vermont) (city)
  11. Vermont (state)
  12. Lake Champlain (attraction)
  13. Hyde Park (Vermont) (city)
  14. Tarrytown (city)
  15. Monhegan Island (island)
  16. Ben & Jerry's (restaurant)
  17. Hudson River (attraction)
  18. Sleepy Hollow, NY (attraction)
2 thankscomments (2)

answered by
Karen from Stonington

If you want the quintessential New England experience, consider a day/night in southeastern Connecticut's town of Mystic, home of Mystic Seaport, the largest maritime museum in the world -- as well as the Denison Homestead Museum, a family farm and home that dates to 1727, -- and numerous other historical sites. 

 Downtown Mystic, as well as the Olde Mystic Village have many shops and restaurants. For some of the area's best food, dine in the pub of the 250-year-old The Captain Daniel Packer Inne or at the farm-to-table Oyster Club. Cap off the evening with a sunset sail on the Schooner Argia with Argia Mystic Cruise or with dessert from Mystic Drawbridge Ice Cream  

Mystic is at exit 90, on route 95, easy to access on your way to Newport. 

Mentioned in this answer:

  1. Mystic (city)
  2. Mystic Seaport (attraction)
  3. Denison Homestead Museum (attraction)
  4. Olde Mystic Village (attraction)
  5. The Captain Daniel Packer Inne (restaurant)
  6. Oyster Club (restaurant)
  7. Argia Mystic Cruise (attraction)
  8. Mystic Drawbridge Ice Cream (restaurant)
2 thankscomments (2)

answered by
Sara from Westerly

I think that your travel plans are very good and thought out. I would say the end of September or the beginning of October would be a good time to travel. I say this just because it can get much colder up north earlier than in most places, and the end of October might be a little to chilly.

As for the last part of the trip, be bold and just drive around and stop at road side things. take in some great views and stop as some local shops that you see along the way. I have found this to be a great thing when traveling. You never know, you might just find that one little place that you want to keep going back to.

Good luck on your travels, I hope you have a great time!

2 thanks

answered by
Karen from Massachusetts

The colors are incredible in New England in late mid to late October.  Provincetown is much much quieter in the fall rather than summer, so you will be able to see more in October. 

Mentioned in this answer:

  1. Provincetown (city)
2 thanks

answered by
Trang from Mont Tremblant

Yeah i agree with you, would recommend to leave Quebec City and Montreal for another trip. I spent 6 days on my trip to Quebec City Montreal and felt it was not enough time. I spend 3 days in Quebec City and 2 days in Montreal and the last day to drive back to Ottawa.

In Montreal i would recommend you do all you're shopping since it has a lot of stores on Rue Sainte-Catherine. In Quebec City spend a lot of you're time patio and dining. Most of the good food is here. For Montreal eating cheap is actually the better option since i find cheaper food in Montreal same quality for less expense. 

Mentioned in this answer:

  1. Quebec City (city)
  2. Montreal (city)
  3. Rue Sainte-Catherine (attraction)
2 thanks

answered by
Bernardita from Santiago

Thanks a lot Melissa and Nathan for your feedback. I have just 15 days total so I think I should leave Montreal for another time and maybe Quebec too.

2 thanks

answered by
nancy from Texas

Depends upon what you like to do and want to see.   I could spend a week in the Bar Harbor and still not have enough time to see and do everything that I wanted. Your itinerary is sort of like being on a will get a "feel" for each place you stop but that's about it. 

Mentioned in this answer:

  1. Bar Harbor (city)
1 thanks

answered by
Christopher from Middletown (Connecticut)

Mostly looks good.  Don't think you need 4 days in Bar Harbor.  I would plan 2 days in Newport Beach, touring the mansions can take up a day by itself.  (And its worth touring the mansions)

September still feels like summer and you can swim in the ocean if you want, October starts getting cool and yes you have a better chance for foliage.  It varies each year depending on how dry (or wet) the summer is but you're driving right into it so you'll have a better chance.  The further north the sooner the leaves change.  New Hampshire will be finished when Connecticut is still at peak.  Bring clothes for weather that can vary from 70's-80's to down in the 40's, especially at night.

Mentioned in this answer:

  1. Bar Harbor (city)
  2. Newport Beach (city)
1 thanks

answered by

I like your itinerary ! Not exactly between New York and the Mall but you are right near the attractions of the Hudson Valley. Lots of historic mansions. .Downtown Tarrytown is nice. Hudson lots of restaurants. Walk over the Hudson River at Poughkeepsie .

Mentioned in this answer:

  1. Tarrytown (city)
  2. Hudson River (attraction)
  3. Poughkeepsie (city)
  4. Hudson Valley (region)
1 thanks

answered by
Patrick from Rotorua

October is the best... Before 15th I suggest.

shop in Montreal the best in the world!!

travel to Tadoussac to see the whales and Ile d'Orleans for some foodie b&bs and that Exceptional French cuisine. pick some apples on the way we have more than 100 kinds in Quebec. 

Mentioned in this answer:

  1. Tadoussac (city)
  2. Ile d'Orleans (island)
1 thanks

answered by
Jason from Boothbay Harbor

Dear Bernadita, I live in near Boothbay Harbor and manage a hotel in that area. Your itinerary looks good. If you're looking for an authentic Maine experience there are several spots in Boothbay Harbor to consider. If you have questions, don't hesitate to contact me.

Mentioned in this answer:

  1. Boothbay Harbor (city)
1 thanks

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