Northeast Road Trip – Summer Vacation 2019

Trip reason:  2019 Summer Family Vacation

Trip length: 10 days

Trip plans: Fly to NYC, drive to The Hamptons, ferry to New London, CT, drive through Maine, and land in Boston to fly home


Atlanta, GA

A typical July 4th for us is spent on Lake Blue Ridge, but this year was a little different.  With an early flight out to NYC, we headed down to Atlanta on the 4th with plans of seeing the fireworks in Centennial Park.  With the help of a good friend at the Westin Peachtree Plaza, we got an upper floor room overlooking the park.  After Cole’s birthday dinner at Atlanta Grille, we ordered room service dessert and watched the fireworks below us and all around us.

Manhattan, NY

After what was an incredible start to vacation, we had a few travel snafus.  We had a AM/PM mix-up on plane tickets and an undesirable rental car experience, but we made it to Manhattan three hours late (actually, 12 hours early given our original plane ticket was for 9:30 PM, not 9:30 AM!!!).  We hoped to be on the road from Manhattan before dark, so we only had a few hours to explore a city that could take DAYS to see.

The Hamptons

We hopped in the car and started our drive to the Hamptons to stay with our friends for the weekend.  This was another destination that could take days to explore the different pockets.  We did some exploration but mostly fellowship.  The entire area was bigger than we had imagined and a lot more neighborhoods and homes.  The bustling shopping and restaurants were in pockets of different towns, such Southampton, East Hampton, Montauk, and Sag Harbor.   While there are plenty of newer multi-million dollar mansions, there’s so much beauty in the historic architecture of homes that have been passed down through generations of families.  With East Hampton being one of the oldest towns in American, there’s a lot of history that comes along with the fine dining and high end shopping that the area has to offer.

An incredible garden center in Bridgehampton, called Marders! We had a blast exploring and Cole got to visit with some endangered species.
Sag Harbor
Montauk Lighthouse “The End” and playing in the public park! This is the oldest lighthouse in New York State and known as The End because it’s at the end of Long Island.  It’s also the eastern most point of the state.  The area is a state park surrounded by public beach area.
Shinnecock Golf Course Clubhouse – home to the 2018 US Open
Cole burying himself in sand at Cooper’s Beach in Southampton

Ferry Ride

From the Hamptons, we took a ferry over to New London, CT to start our trek up to Maine. On the drive over to the Orient Point Ferry, we went through North Fork, Long Island, which is rural wine country full of vineyards and farm stands.  I would like to come back and explore this area.

Portsmouth, NH

From New London, we started driving and driving.  Our first stop was at Portsmouth, NH.  We strolled through town.  It had a rather large downtown area with shopping and restaurants.  We landed at the Portsmouth Brewing Co. for lunch.  We didn’t find a beer we loved but the food was fantastic.  Paul’s shrimp wrap was perfectly seasoned and they mastered crispy chips and layering nachos.  Cole had a pizza (boring, haha).

Freeport, ME

We decided to take the scenic route up to Freeport, ME to visit another friend who Paul met through the rental industry.  This route was interesting.  We went through a small stretch shown in the pictures below that were extremely congested, beautiful views of the coast, and tons of little motels along the road.  Our scenic route didn’t last very long, given that it was taking forever and each little town looked very similar.  We were going to stop at the very popular Kennebunkport, ME, but we ran out of patience.  Think two-lane road in high tourist season … pace of a snail getting anywhere.

We stopped at Freeport (north of Portland) to visit our friends, Justin and Lisa.  Justin took us out on his boat, and we cruised past some beautiful homes, historic spots, and saw the coast of the City of Portland.  It was a treat!

Boat ride!


Casual dinner at the yacht club – fried shrimp & scallops, lobster roll, clam chowder, haddock sandwhich + plus Gifford’s ice cream (our fav!!)

We stopped at THE L.L. Bean store in Freeport the next morning.  It is located in a downtown area with a large space for the main retail store, an outdoor park with a stage (they host free yoga each morning during the week), and the home store.  In this same area were many outlet stores.  All the buildings fit the area and weren’t out of place at all.  Props to the town for making the development look great and to L.L. Bean for being awesome for a community!


Camden, ME

After doing a little damage, we hit the road for Bangor, ME, which was intended to just be a sleeping spot.  We had grand plans for driving up to St. Andrews, BC.  However, in reviewing the drive time and taking Justin and Lisa’s suggestions, we changed plans.  We drove through Boothbay and landed in Camden for lunch.  Camden was another cute town with shopping and restaurants on the coast (a little less congested).  We ate at Waterfront.

Before leaving Camden, we drove up to Mount Battie.  There is a small fee to enter the state park, but worth the panoramic views of the area.

Bangor, ME

After what seemed like days of driving, we made it to Bangor.  No one was really excited about this stop, and we had been advised there wouldn’t be much to do.  Stayed at Fairfield Inn & Suites, which was located about a mile from downtown Bangor.  We did a drive-by the downtown but didn’t make it back.  However, we had a great evening.  We played putt-putt at Blackbeard’s and also got more Gifford’s ice cream!  We decided to eat dinner at the hotel at this cute restaurant called Timber, and wow! It was delicious!  Oh yea, Bangor is home to the Paul Bunyan statue…

Downtown Bangor at night

Bar Harbor, ME

Bar Harbor is a beautiful destination.  We gathered that a lot of people come for several nights, but we just did a day trip.  Save time to walk around and explore the little shop.  We started with with lunch on the water at Stewman’s.

Our whale watching trip started in the afternoon and lasted for 4-5 hours.  We wer on a boat with several levels, and we recommend sitting in an enclosed space.  When you’re moving, it gets cold, despite inland tempuratures being in the 80s in the summer.  We were all in sweatshirts and still chilly.  When you get out to the whale watching areas, you can migrate around the boat.  We spotted 7-8 whales on our trip.  They sell some snacks, but you can bring your own.  Be prepared for a full afternoon on the boat.  It was a beautiful ride.  One of the whales breached, but we didn’t see it.  The whole experience is unique.

After the whale watching, we drove a few miles up to Cadillac Mountain in Acadia National Park.  There’s so much to do in the Park, but this all all we had time for.  It was gorgeous and only took us about 45 minutes up and back down.We found a road side “shack” for dinner, and as we expected, it was some of the best from our trip!  You’ll notice how huge the chunks of lobster are in the lobster roll.  The clam chowder won the best from our NE trip.  Oh, and that blueberry pie!!!!

Boston, MA

From Bar Harbor area, after our delicious road side meal, we started the drive to Boston.  It was about 4.5 hours and we were later in the day.  We arrived after midnight into the city.  We stayed at the Courtyard Boston Downtown located on Tremont St. and conveniently located to Boston Common.  This was a really unqiue Courtyard in a historical building.  It was very artistic.  We loved it!  Our room was spacious and comfortable.


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