The Ultimate 2 Weeks Road Trip from NYC Through the East Coast to Canada

Quite simply, if you are one who likes to go on a vacation at your own pace, loves freedom and flexibility, prefers visiting places off the beaten path and enjoys the journey as much as the destination, you will love road trips.

Taking a road trip means different things to different people. Road trips are definitely not for those who can’t stand driving long distances and who hate getting lost.

Travelers like Trippy member Bernadita Cruz from Santiago Chile knew exactly what she wanted when she asked for advice. Her dream is to visit the small towns instead of big cities in New England. She also wants a taste of French Canada. Her starting and ending point is New York City.

Here is what she wrote:
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)
Provincetown - 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!!!

I am going to craft out a sample itinerary for her based on her questions and preferred destinations.

The road trip itinerary:

Day 1 NYC

Arrive in NYC, free day to explore the city.

Note: If you are flexible with your hotel, I suggest staying outside of Manhattan, preferably a place close to the interstate and where parking is available yet close to Manhattan. I would suggest Fairfield Inn Long Island City, located just off I-495 with parking spaces ($28 per night) available for guests.

Fairfield Inn Long Island City provides a complimentary shuttle service to and from the hotel to the closest subway station. It takes 20-min to get to Manhattan from the subway station.

Day 2 Newport

Depart NYC for Newport. Drive 180 miles to Newport RI. It takes about 3 to 4 hours to drive depending on the traffic conditions. Try to avoid rush hour and start your journey before 6 a.m. or between 10 a.m. to 3 p.m.

For things to do and places to stay in Newport please go to Discover Newport, the official tourism website of Newport.

I suggest a three day, two night stay in Newport.

Day 3 Newport

Full day to explore Newport.

Rhiana Desmarais from New Hampshire suggested:
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.

Day 4 Provincetown

Start your journey early. Drive for 119 miles to Provincetown. Provincetown is located at the tip of Cape Cod. Your journey may take longer as pointed by Trippy member Missy Johnston from Newport:

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.

Some of the things to do in Provincetown:

Visiting Truro Winery
Bird watching
Enjoying beach activities

Day 5 Nantucket and Portland

Check out early from your hotel, drive 47 miles to Hyannis and board the one-hour high-speed ferry to Nantucket. Spend a full day in Nantucket and return at around 7 or 8:45 p.m. by ferry to Hyannis.

For things to do in Nantucket, here is Wilson Patton’s suggestions:
Check out ice cream at The Juice Bar but go at off hours to avoid the lines. 10b, also known as Ladies Beach, is a great place to find some waves. American Seasons is delicious for dinner, and I would highly recommend it. Renting a bike is not a bad idea because Nantucket is a beautiful place to ride around!

Important Hyannis ferry information:
Information and ferry schedule from September 6-October 11, 2016
Hyannis Ferry parking and fees

Traveling late in the evening from Hyannis to Portland (Maine) may be the best way to avoid heavy traffic. It takes about three hours to drive in normal traffic conditions. I suggest staying at the Courtyard Portland Downtown/Waterfront. You are within walking distance to the Old Port district and parking at the Courtyard is $18 per night.

Day 6 Portland and Bar Harbor

Eat lobster in one of the lobster shacks in Old Port district before heading out to Portland Head Light (Maine’s oldest lighthouse) in Cape Elizabeth. After a quick stop, drive north to Freeport (Maine) (21 miles away) for shopping at LL Bean flagship store.

Depart for Bar Harbor after shopping. Bar Harbor is 158 miles from Freeport. Nathan Platt from Vermont wrote:
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 when you're driving up the coast of Maine . L.L.Bean mothership store is there and it's a great shopping town.

Day 7 Bar Harbor

Relax for three days and two nights in Bar Harbor. In Bar Harbor you can hike, fish, golf, camp, shop or sample local craft beer.

Trippy member Jane Scoles has a list of places to stay and things to do when in Bar Harbor:
I have stayed in several places in Bar Harbor they are...Edenbrook Motel, Acadia Inn, The Days Inn Bar Harbor/Frenchman's Bay and Isleview Motel and Cottages. In the summer there is a shuttle bus called the Island Explorer that picks up visitors at many of the motels and will take you to downtown Bar Harbor or Acadia National Park. The motels a few minutes out of Bar Harbor are cheaper but the shuttle can take you where you need to go. I'd check with the motel to see if they use the shuttle. The rides are free. I hope this helps. If I can be of any more help let me know.

Note: For things to do in Bar Harbor please visit

Day 8 Bar Harbor

Full day to explore Bar Harbor.

Day 9 Quebec City

Leave early in the morning from Bar Harbor to Quebec City. Your drive is around 275 miles today and you will have to go through border crossing from the US to Canada.

Here is a checklist before you leave for Canada:

  1. Have your valid passport ready. Make sure you have the proper entrance visa if needed to visit Canada (applies to non-US citizens).

  2. According to Avis car rental company: With advance arrangement and consent from Avis, certain cars may be rented from the United States and driven into Canada by U.S. residents. A Canadian non-resident insurance card may be required and is available at the Avis rental location. Please call 800-230-4898 for more information.

  3. Have a valid driver’s license. Here is what Budget car rental says about driver’s license for non-Canadian and non-US citizens: Non-U.S. and non-Canadian residents are required to present a valid driver’s license and a passport from their home country. If the information on your driver’s license is not written in the Roman alphabet, you must also present an International Driving Permit. If you have indicated on your reservation that you are a non-U.S. resident, you must also present proof of your return trip back to your resident country or your confirmed reservation rate will change. 

  4. Certain fruits and vegetables are not allowed into Canada. To avoid delays, don’t carry fresh produce in your vehicle.

  5. Read Traveling between New England and Canada for detailed information.

You’ll be going on Route 201 to the Jackman/Armstrong border crossing.

Trippy member Scott Mahaffy from Fort Collins suggested the following place to stay and things to do while in Quebec City:
Stayed at the Fairmont Le Château Frontenac. Honestly, we signed up for the Fairmont credit card and, after $2,000 spent over three months, received President's Club status. We received two free nights at any Fairmont in the world. We stayed three nights and paid for one. With our status, they upgraded us to the gold floor.

Tony Bourdain was spot on with his recommendation to L'Affaire est Ketchup. Outstanding! We also had a great lunch at La Galette Libanaise.

Must see would be the La Citadelle de Québec, the farmer's market, and a stroll on Rue Saint Louis out to Grande Allée. Kind of a mini Champs Elysee. They also have some decent street performers, most of which take their turn around the statue of Samuel de Champlain.

Roxanne Cormier from Montreal added:
The problem would be, would you have enough time. There is so much to see in Quebec City. You cannot mist the Vieux-Québec (old city). You will have lost of choices at all ranges of $$. Leave you usual fast food chains aside. Live a little experience good food and historical landscapes. Try one of the nice restaurant in the steps going from the Vieux-Québec to the Basse-Ville (original site of the city during colonisation). Another street with lots of good choices is Rue Cartier. If you don't have a place to stay yet, try Relais Charles-Alexandre ( go on Internet for there site) on Grande-Allée E near Rue Cartier. It several transformed joined buildings into a Inn, with cackeling floors, breakfast included. Very nice ! I used to go there frequently for work. It's within walking distance of Vieux-Québec.

Day 10 Quebec City

Full day to explore Quebec City.

Day 11 Montreal

Leave right after breakfast for your 157 drive from Quebec City to Montreal. You will arrive with enough time to explore the city in the afternoon and evening.

Here are four hotels suggested by Trippy members:

1. Hotel St Paul boasts simple and comfortable rooms. The perfect place to return to after a busy day of exploring Montreal.
2. Hotel Le St. James has a European atmosphere you don't find much in North America. The staff are professional and the rooms are impeccable.
3. Hotel Gault's minimalist design really makes it stand out among the old-world architecture of the neighborhood.
4. The elegant Esthétique La Quintessence Inc sits next to Lake Tremblant. Each room has a wood-burning fireplace and balcony. It's especially beautiful with snowfall.
Essential in Montreal: Vieux-Montreal, Mont-Royal to get the city view, Saint Joseph's Oratory of Mount Royal, Olympic Stadium, Jardin Botanique (those two are close), Saint-Laurent, St Denis St and Mont Royal Blvd (lots of restaurants, bars and stores).
Two smaller hidden streets which have great restaurants: Rue Prince Arthur and Rue Duluth.
Other options: Casino de Montréal, Chinatown, Place des arts, Underground City (which is basically stores).

Day 12 Montreal

A full day to explore Montreal

Day 13 NYC

Leave Montreal early for NYC to have enough time for shopping at Woodbury Commons Premium Outlets before returning to your hotel in NYC. It is about 370 miles from Montreal to NYC.

The Autoroute 15 will take you to the Lacolle/Champlain border crossing. This is one of the busiest crossings between Canada and the US.

The shops at Woodbury Commons close at 9 pm. Woodbury Commons is about 55 miles from NYC.

Day 14 NYC

Full day to explore NYC.

Day 15 Depart

Leave for home.

The late Jesse Owens, an American Olympic gold medalist once said: We all have dreams. But in order to make dreams come into reality, it takes an awful lot of determination, dedication, self-discipline, and effort.

Road tripping and sticking to an itinerary takes determination, dedication, self-discipline and effort. Do you have a dream road trip you want to take? Let us help you craft out an itinerary. Post your questions on Trippy and if you aren’t a Trippy member yet, here are 3 easy steps to join:

  1. Log in to your Facebook account.

  2. Sign up to use Trippy using your Facebook account.

  3. Receive a confirmation via email from Trippy and verify your email account.

That’s it! See you there.

Article by Claudia Looi

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