Friday Family Vacation: New England Road Trip with Points


Our Friday Family Vacation is a New England road trip with points written by Megan Condello, our lovely THM Digital Business Manager.

Living on the East Coast, a family road trip through New England is a dreamy way to spend your summer vacation. We spent almost 2 weeks in August traveling in our minivan with three kids on a road trip from Boston to Prince Edward Island, Canada. The first leg—from our home in Upstate NY to Boston, through New Hampshire, and up to Maine—was the perfect 5-day New England road trip itinerary.

Alternatively, you could fly into Boston (BOS) and pick up a rental car to complete this New England road trip through Boston, New Hampshire, up through Maine, and onto Prince Edward Island. If you plan to just spend time in Boston, THM has that covered in this Boston blog post.


Boston Hotels and Things to Do with Kids

Once we arrived in Boston, we checked into our hotel for the next 2 nights. We stayed in a standard room at the Hyatt Centric Faneuil Hall Boston. We booked our 2 nights for 23,000 points per night by transferring Chase Ultimate Rewards to Hyatt.

My husband had work meetings on our first day in Boston, so the girls and I headed out to explore Quincy Market, ride the Rose Kennedy Carousel, walk the Long Wharf, visit the New England Aquarium, Old State House, and Old South Meeting House. The Hyatt Centric gave us a great location to be able to easily walk to all these sites.

The next morning, we bought tickets for the Hop on Hop Off Trolley Tour and spent a bit of time touring the USS Constitution and checking out their wonderful, kid-friendly visitor center.


Mt. Washington, New Hampshire

Our next stop on our New England road trip was to drive through New Hampshire towards the White Mountains of Mount Washington. We stopped here to ride the Steam Cog Railway up Mt. Washington. This is a steam train that goes up the mountainside. This Mt. Washington Cog train is the World’s First Mountain Climbing Cog Railway and the 2nd steepest. It has been running for more than 150 years!

We didn’t stay overnight in New Hampshire, but there is an Omni nearby in Mount Washington that looks dreamy—the Omni Mount Washington. This hotel is bookable through using the Amex Platinum Fine Hotels + Resorts credit. I’ve added it to my list of places to return to someday. I bet this area is absolutely beautiful in the Fall during leaf-peeping season.


Mt. Washington Steam Cog Railway, perfect stop on a New England road trip

Steam Cog Railway

Acadia National Park with Kids

After our day riding the cog train up Mt. Washington, we headed to Rockland, Maine to visit with friends. (side note: the Rockland Lobster Festival is hosted here every summer. Sadly, we were there the weekend before the festival and had to miss it.) After spending a few hours with friends, we headed to our next overnight stop, Bar Harbor, Maine. We stayed at the Acadia Inn for 2 nights, paying $582.46 cash total.

We checked into the hotel after dinner and went right to bed so we could be up early for our 8am reservation to visit Cadillac Mountain inside Acadia National Park. This has to be reserved ahead of time through the National Park Service and does sell out! We spent all day inside the park, walking the trails and enjoying the natural beauty. Acadia National Park is definitely a top spot to visit on a New England road trip.


Acadia National Park - New England road trip


Prince Edward Island, Canada

After our 2 nights in Maine, we headed to Prince Edward Island, Canada! If you’re a fan of Anne of Green Gables, there’s no better place to take a family road trip than PEI. Fans of the book can take a family road trip through Prince Edward Island, exploring the places that inspired the famous novel. This beautiful island is the birthplace of author Lucy Maud Montgomery and the setting for Anne of Green Gables. With its charming red sand beaches, rolling hills, and quaint towns, Prince Edward Island was a perfect stop for our family of bookworms.


White House with children standing outside - Anne of Green Gables New England road trip


Charlottetown Hotels

We spent five nights in Charlottetown, staying at the Delta Hotels Prince Edward. We booked this hotel with Marriott points, getting the 5th-night free deal. It cost us about 160,000 Marriott points. This hotel has a heated indoor pool, a fitness center, and a restaurant on site. The location is amazing to be able to walk almost everywhere within Charlottetown village. The rooms were rather large, comfortably fitting our family of 5.


Charlottetown, Prince Edward Island

The capital city of Prince Edward Island is Charlottetown. This is where we based ourselves for our 5 days on the island. There are plenty of things to see and do within walking distance of our hotel. You can walk to the Confederation Centre of the Arts, which is home to a beautiful theater and the Anne of Green Gables Musical. Take a stroll along Victoria Row, a pedestrian street lined with shops and restaurants. Visit the Beaconsfield Historic House and Gardens and enjoy a meal at one of the many restaurants in the city.


Playbill for Anne of Green Gables


During our 5 days in Prince Edward Island, we also went on a whale watching/deep sea fishing tour, checked out a number of lighthouses, visited the Green Gables Heritage Place, got chocolates from Anne of Green Gables Chocolate Factory located in Avonlea Village, had ice cream from Cows Creamery, and swam at the beaches of Prince Edward Island.

After our wonderful 5 days in Prince Edward Island, we started our long drive back home. We stopped in Bath, Maine overnight, staying at the Residence Inn Bath Brunswick Area. We booked this night with a Marriott free night certificate.


Bottom Line

Megan’s New England road trip with points sounds delightful to me. This is an area of the United States many of our readers would enjoy and something I need to add to my “to-visit” list. Thanks for sharing it with us for our Friday Family Vacation to New England.

Green field with white building in distance

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