The Road Trip Every New Yorker Should Do At Least Once

SomesvilleRumors have it that our new mayor has dropped the groundhog on his head and as a result we are suffering through the worst winter in recent memory.  Major salt shortages all over the city.  Lower back spasms from all that reaching to the wallet to pay the shovellers.  And not so much eating out lately.  Quality of life is taking a hit due to this winter, and instead of the usual food porn I’m presenting you with the finest New England lighthouses and pretty bridges with flowers.  Yes, the inner Ziggy is out at it again.

With that said, I was asked quite a few times for that New England road trip we did a few years back, and I figured its time to put it up here.  This is an 11 day road trip showcasing some NE highlights.  If anyone has any suggestions/comments/threats please dont hesitate to share in the comments.  But overall, road trips out of NYC dont get any better than this (and we had our share which includes Niagara)

The short Version (1 night each unless noted):



Bar Harbor – 3



Gloucester – 3

Day 1 – Newport, RI.  One night.  Along with the drive back home this is the longest drive of the trip.  You are here to see the mansions, the gigantic summer cottages where the wealthiest Americans came to play in late 1800’s, early 1900’s.  You have just enough time for a couple of mansions on day one.  Allow around 75 minutes in each.   The Breakers, Elms, Marble house and Rosecliff are the musts IMO.  Consider the behind the scenes tour at the Elms.  Breakers stays open later in the day so you can squeeze it in the first day.  Have dinner in Salvation cafe.  Save your money and spend the night somewhere in Middletown very close by.  There’s a Holiday Inn express among other chains.

Newport, RI

Day 2 – Morning in Newport, and off to Maine.  Visit the rest of the mansion you want to see and do the spectacular cliff walk.  Park somewhere on Narraganset ave and walk to your right and back.  Visit the Touro synagogue, the oldest in the USA (1763).  Not the most beautiful and not the most interesting tour, but it will make you look good at future cocktail parties.  Take a drive on Ocean ave and have lunch in one of the wharf’s.  Black pearl is decent.  Good clam chowder.  Overall, Newport is fairly touristy (for good reason) which means not the most exciting food town.  After lunch start driving toward Bar Harbor with the idea of spending the night somewhere in the middle.  Hampton Inn in Saco near the highway is a good cheap option for families.  On the way to Saco however if its a nice clear day, take a detour to Cape Neddick to see the striking Nubble Lighthouse.  Stop by at the famous Clam Shack in Kennebunkport for a lobster roll on the way to the hotel.

Day 3 – Drive to Bar Harbor.  About 3.5 hours from Saco or Portland.  Take the 295/95 route and leave the scenic route 1 to the way back.  A convenient lunch in the area is the Chart Room off the main road.  This is a good day to simply relax and enjoy your hotel and Bar Harbor, but also a good day to go on a lobster tour with something like Lulu lobster because the rest of the days you would want to stay out of the area as much as possible.  Its a good day to start your lobster meal marathon somewhere although I dont have a particular recommendation.  Last time we had  lobster crapes at Maggies but looks like its now closed.  Have lobster ice cream at Mount Dessert Ice Cream.  Again, for the purpose of future cocktail parties (“Darling, you should have seen all the crazy gelato flavors being scooped up in Rome these days.. Anchovies! Feh! “, “Well, I bet it still beats Lobster gelato in baa haaba, my dear”).  You get my point.

Lulu lobster

I recommend splurging at the Bar Harbor Inn for 3 nights.  Spectacular setting, old rustic hotel with a lot of charm.  While there, please tell them to stop emailing Ziggy promotional material.  I will revisit when I’m ready.  Thank you!

Bar Harbor inn

Day 4 – Explore Acadia.  Essentially you want to do the 27 mile Park Loop road that takes you to all the cool spots.  Start with the visitor center and get a map.  Stop at Sand Beach, Thunder Hole, and other stops on the route.  Have lunch at the Jordan’s pond (get the popovers, good lobster rolls).  This is a must.  You will be hard pressed to find a more stunning setting, in the park’s only restaurant.  After lunch or before take a walk around the pond.  Then climb the South Bubble on the other side of the pond for more incredible views.  Drive up Cadillac mountain and walk around the summit and stay till sunset.  Its cold up there so bring a sweater, or a jumper if you are British.

South Bubble

Day 5 – Perhaps my favorite day of the entire trip.  Explore the quiet side of Mount Dessert Island:  Got to Somesville and look for the bridge (top picture).  Go kayak on Long pond, take a swim at stunning Echo lake beach, visit southwest harbor, do the ship harbor trail, and look for bass lighthouse.  “But Ziggy I still don’t see why this is your favorite day” Have lunch at Thurston’s lobster pound in Bernard.  “Ahh. thank you!”

Thurston's lobster pond

Day 6 – Back on the road.  Time to hit Route 1 – Not the most scenic drive, but all sorts of interesting stops on the way.  Consider spending some time in Camden.  But right before you get to Camden drive to the top of Mt. Battie for some great views of the bay.  Not a strenuous climb by any means.  In Camden enjoy the various galleries, shops, etc and you can take a 2 hour Schooner cruise if you like from the various vendors lined up at the port.  Have lunch in Camden or area.  Continue driving on route 1 south.  Another spectacular lighthouse on the way is the light at Pemaquid point.  Spend the night in Boothbay harbor, and consider dining at, what else, the lobster dock.

Pemaquid lighthouse

Day 7 – Back on the road.  Visit the surprisingly majestic and serene Coastal Botanical Gardens.  Its huge, so you can easily spend half a day here if you like.  Walk the forest.  Continue to Freeport and visit the original LL Beans store.  They have all kinds of activities and clinics you can sign up for in advance like archery and canoeing.  Spend the night in Maine’s largest city and one of the greatest food towns on the east coast, Portland.  Consider dining at Street and Co. or its sister Fore Street, widely considered as one of the best restaurants in the USA by all the publications/lists out there.

Coastal Botanical Gardens

Note:  If you opt to stay longer in Freeport to take advantage of the LL Beans clinics and still do the botanical gardens, you may need to stay an extra day in the Portland area or adjust the itinerary as needed.

Day 8 – Visit Portland sites including and especially Portland Light (yes another lighthouse – what else is new, but this is an absolute must).  This is more of a giant sprawling park that attracts a lot of locals and tourists and offer some of the best photo opps of the trip.  Its been over 12 hours since the last lobster meal so lunch at the nearby The Lobster Shack at Two Lights.  Drive toward Glaucester, Mass via Kennebunkport and the popular summer resort Ogunquit.  The idea here is to stay 2 nights in or near Gloucester.  Consider staying at TownePlace Suites in the town of Danvers.  Cheap 2 BR units right between Gloucester and Boston for easy access to both.  I found that the Gloucester popular hotels sell out quickly and/or too expensive for this purpose.

Portland Light

Day 9 – Take the 4 hour whale watching trip with 7 Seas Whale Watch out of Gloucester.  Should be one of the highlights of the trip.  Reserved in advance.  We saw 11 whales last time.  Or one whale 11 times.  Either way it was a blast

Note:  The summer is the best time to see whales in the area.  In order to play it safe weather wise you could do the Gloucester leg of the trip on the way to Maine instead of back, and switch if necessary in case the weather turns resulting in choppy water.

7 seas whale watch 7 seas whale watch Gloucester

Day 10 – Visit Gloucester sites including the various monuments, Hammond Castle, the nearby Rockport and do not miss Motif Number 1, the most often-painted building in America.  And in case it looks familiar and you feel like you’ve seen it a hundred times, you did.  When your kids watched “Finding Nemo” over and over again.  Its one of the paintings at the dentist office.  Have lunch in Causeway (good haddock) and check out Halibut point park

motif no 1 Rockport

Day 11 – Visit Boston

More from Acadia…

Echo lake beach Long pond Cadillac Mountain Sunset Cadillac Mountain Acadia - Sandy Beach Jordan's Pond Jordans Pond

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4 thoughts on “The Road Trip Every New Yorker Should Do At Least Once

  1. Really enjoyed looking through your photos on this dreary NY day! I love Maine but haven’t been there forever, might be time to make another trip soon!

    • Thanks Kristin. By the time I finished writing this I convinced myself to go back next summer. This blog is costing me a lot of $$$$

  2. Marg

    I’ve often thought about going to Maine but wasn’t sure it was worth the drive. After reading your blog and seeing the pictures, you’ve convinced me!
    How about exploring Nova Scotia next summer instead!? It’s beautiful here too!

    • Yep, Nova something to consider as well. Its just a little too far for us. I have to admit the older I get the more I want to return to familiar places (hence all the provo trips). I still hope to make it to Banff tho.
      We were looking at one of those NE-Canada cruises before but didnt quite like what we saw. One day…

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