Road trip guide from the Southeast to Maine

January 20, 2016
Road trip guide from the Southeast to Maine

Road Trip Guide from the Southeast to Maine

We took this awesome road trip in 2011 but all of the information is still relevant.  Our trip was based around dropping my son off at camp in Pennsylvania and our trip took about ten days.  I don’t like road trips where you go from point A to point B on the freeway without stopping to really see everything.  We were in a different city every night so the travel time each day was usually about two hours, except for the first and last day.  Although that could also be modified if you have more vacation time to work with.  We live in the Atlanta area so the drive time on the first day was long but everyone had vacation excitement so the time in the car really didn’t seem bad.  Also, I suggest having a clipboard with all the states listed so you can all look for license plates and mark them off.  That is surprisingly fun and keeps everyone occupied.

Day one:

Our first destination was Chincoteague Island, Virgina.  It is about 700 miles / 10.5 hours from Atlanta and mainly on the freeway.  This is about the only portion of the trip that is on the boring freeway, the remainder is beyond scenic!

Chesapeake Bay Tunnel Bridge

Chesapeake Bay Tunnel Bridge

One exciting point was the Chesapeake Bay Bridge Tunnel.  I was so excited to see this.  It’s very cool to drive on a bridge then a tunnel and it kept going like that.  We stopped for lunch on the bridge at Chesapeake Grill.  Also, there is a nice fishing pier so you can walk a bit and get some fresh air.  From the bridge the drive is only about 70 miles to Chincoteague Island.


The view from our balcony at the Anchor Inn.

We stayed at Anchor Inn.  It is on the Chincoteague Channel and our balcony overlooked the water and boat docks.  The hotel is nice with a very casual comfortable feeling.  The continental breakfast is served in a little building with a nice porch.  We met the nicest people there.  The hotel is within walking distance to some very cute shops in town.  We traveled to Assateague Island National Seashore in the late afternoon. It is really an amazing beach that is known for wild horses.  We were not lucky enough to see them but we did encounter gigantic mosquitoes.  Take me serious and bring something to combat them. I’m from the south and know mosquitoes but these take the cake.

Beach in Assateague

Assateague Beach

Day two:

Our goal on day two was to make it to Atlantic City!  It sounds far but no worries it is easy and the drive is amazing.  Trust me.  It’s along the Delaware coast.  I was so surprised at the beauty of the beaches and the beautiful homes that the drive just flew by.  We stopped at Rehoboth Beach, it is awesome.  The waves were much stronger than Florida waves and the sand was much rougher with rocks or shells or something.  We looked like we had never been to a beach before and were knocked down as soon as we stood up.  Those pictures aren’t being shared on this blog.  We left the beach and went to Lewes, Delaware.  We took the Cape May-Lewes Ferry to Cape May, NJ.

on the ferry from delaware to jersey

The drive from Chincoteague Island to Lewes was only 81 miles / two hours which is why we had plenty of time to stop for lunch and the beach.  The ferry was only about $80 if I remember correctly for our big excursion and four of us.  The ride is about 85 minutes on the ferry to travel 17 miles to New Jersey.  The ferry is comfortable and fun with plenty of seating outside or inside.

Cape May - Lewes Ferry

Once we arrived in Cape May we drove about 65 miles to our hotel in Galloway, NJ (just outside of Atlantic City).  We stayed at the Stockton Seaview Hotel & Golf Club.  It sits on 670 acres and has two 18 hole golf courses.  It is elegant, it is beautiful…and I loved every minute of it.  It is a short drive to the boardwalk in Atlantic City. My kids loved the rides on the pier.  It was a good time for sure.

Atlantic City Boardwalk

Day three:

Our goal on day three was to get to NYC!!  The driving distance was 116 miles.  We stopped at Liberty State Park.  The view of NYC and The Statue of Liberty is amazing from here and definitely worth stopping for!  It was our first trip to NYC and we loved it.  We stayed in Times Square at the Crowne Plaza.  It is a very nice hotel and the location is ideal!

Statue of Liberty from New Jersey

in jersey looking_at_nyc

Day four:

Our destination was Newport, Rhode Island.  The drive was a little longer, the distance was 179 miles.  It was mainly on the interstate through Connecticut.  I don’t remember the name of the hotel we stayed at in Newport but really there are so many beautiful ones to choose from that I’m sure whichever you choose will be great.  We spent the afternoon at Newport Beach at the playground.  Be sure to go on the ten-mile drive, the homes are beautiful.

Newport RI

Newport RI

Day five:

Our destination was Gloucester, MA.  The drive was 110 miles but we stopped in Boston for the afternoon first.  Boston is about 70 miles from Newport.  We spent the afternoon at Boston Common at the frog pond and the swan boats.

Boston Common Swan Boat

Boston Common Swan Boat

It is a very beautiful place and a nice way to spend a few hours.  We stayed at The Colonial Inn Bed and Breakfast in Gloucester, MA.  I would highly recommend this bed & breakfast. The room was huge with two double beds and a twin.  The atmosphere was lovely.The location is just two blocks from Niles Beach.

The Colonial Inn in Gloucester

Niles Beach in Gloucester

Niles Beach in Gloucester



Day six:

We traveled to Kennebunkport, Maine and the driving distance was 86 miles.  We stopped in Portsmouth, New Hampshire to eat lunch and tour the downtown area.  We stayed at the Nonantum Resort in Kennebunkport.  It is casual, it is historic and it is very elegant.  It sits on the Kennebunk River with a huge lawn between the resort and the river.  They have amazing activities for kids in the evenings.  My daughter participated in a Pirate and Princess party which she totally loved.  The rooms are big and pretty!  More importantly the staff is amazing.  This resort was so comfortable and everyone was so friendly.  My son and I rented a kayak the next morning.  Neither of us had been in a kayak before and I was certain we would end up in the river swimming but we were just fine.  It was so peaceful and quiet.  Later that day we went out on a lobster boat.  We loved that also, it was fun and informative.

on the lobster boat

The beach is a short walk from the hotel and it’s very nice.

riding bikes on the beach in Kennebunkport

My son and I saw the Secret Service Agents on their raft boats coming from the Bush Compound.  That was kinda cool.  We saw the boats again when we were on the kayak.


The Bush home. We saw this from the lobster boat

When it was time to leave Kennebunkport I literally shed a tear.  I wanted to stay so much longer and will definitely return sooner rather than later.

Day seven:

This was a longer drive day and mostly on interstates at we headed to Bennington,Vermont.  The distance was 192 miles.  I don’t remember the hotel in Bennington but it was very nice.

Day eight:

Our goal was to get to Camp Woodward in Woodward, Pennsylvania.  There are a few different ways to get there from Bennington but we chose the route that was about 333 miles.  If your child is interested in BMX, skateboarding, film, photographer, cheer or gymnastics they would probably love Camp Woodward.  My son went for two weeks for two summers and he loved it.  The camp is amazing.  It’s in the heart of Amish country and it is beautiful.

Day nine:

We drove straight back to Atlanta which was very, very long and boring.  Ideally we would have stopped in a couple more cities on the return trip but work called and they expected me back.  The nerve.  The year before we stopped in Hershey, Pennsylvania which was awesome!

I hope you like this road trip.  It was great and I would do it again in a heartbeat. I truly do believe that you would like the hotels listed.  I’m pretty picky about hotels and I loved them all.  If you take a road trip similar to this I would love to hear about it!  Happy travels!


Road Trip from the Southeast to Maine #roadtrip #maine







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  • Reply Cindy harris January 20, 2016 at 8:40 pm

    Such a great trip & beautiful scenery. Would love to go again, would like to adventure on into Maine.

    • Reply fabulousindeed January 21, 2016 at 8:11 pm

      Yes a road trip to completely explore Maine would be great!

  • Reply Old bitter teacher January 20, 2016 at 5:23 pm

    I want to go on that trip! Do you offer travel services? You should; you seem so knowledgeable about it all.

    • Reply fabulousindeed January 21, 2016 at 8:10 pm

      Thank you! You should go on this trip, you would love it!

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