East Coast Road Trip: Enjoy the Summer in New England

This summertime East Coast road trip starts off at the Thimble Islands of CT and ends in Cape Elizabeth, Maine, hitting every summer-perfect sight along the way. New England is beautiful in the summer and the farther north you go, the more pleasantly cool it will be, so it’s a great escape from the steam-bath that the rest of the U.S. becomes in the summer (except for the desert, which is more like a sauna).

Portland Head Light

In fact, it gets so cool the farther north you go, you’ll need to pack a sweater! Check out my coastal road trip packing list for more tips about what to bring on this East Coast road trip. Besides being cooler, what this trip offers is the quintessential American icons of summer including beautiful islands and beaches, sailing races, dunes, lakes and water sports, hiking, and lighthouses.

The more time you have for this trip, the better, as I’ve packed in a lot of places to see. Pick and choose if you’ve only got a week.

East Coast Road Trip – Stop 1
Thimble Islands, Stony Creek, CT
Suggested Number of Days: One Day
Start in the charming town of Stony Creek where boat tours launch regularly to view the Thimble Islands. I highly recommend Captain Bob’s tour on the Volsunga IV. He’s extremely entertaining as he tells many funny, racy, and interesting stories about each island.

The islands are made of pink granite bedrock and the islands as well as the whole shoreline are gorgeous. Each island has one or more homes built on it. Generations of families have lived on these islands accessible only by private boat and cut off from electricity and running water until recent years. It’s fascinating to see the lives they’ve made there.

East Coast Road Trip – Stop 2
Newport, RI
Suggested Number of Days: Two-Three Days
Enter the heart of the sailing world in Newport. Although people usually think of the famous mansions when they think of Newport, the deeper underlying truth is that this town is a Mecca for sailors. From the moment you arrive until you leave you will see sailboats wherever you look, regattas in progress with colorful spinnakers unfurled, and the sailors themselves, dark from the sun and rugged-tough the way that a body-builder will never be.

Besides watching sailboats, what should you do?

  • Newport Mansions – The mansions are a given as they are so famous and awe-inspiring to see. It’s hard to believe these giant palaces were considered "cottages" by the robber-barons of the 19th century who had them built as summertime retreats. My favorite is Rosecliff – you can easily see that Versailles was the inspiration for this gorgeous showplace.
  • Cliff Walk – Although you can see the mansions from this 3.5 mile long cliff-hugging trail, this path’s main benefit is the outstanding views of the ocean, and, yes, more sailboats!
  • Gansett Cruises – Take an evening cruise and enjoy a champagne toast at sunset and a delicious seafood dinner while getting some time on the water. The people that run these cruises are very friendly and knowledgeable about the area, telling stories and offering advice if you plan to spend more time in Newport. To top it off, the cruises are dog-friendly so if you’re bringing your dog(s), they’re welcome aboard.
East Coast Road Trip – Stop 3
Nantucket, MA
Suggested Number of Days: One if Day Trip, Two if Staying Overnight
Leave your car behind for a day trip to Nantucket, taking the Fast Ferry from Barnstable Town, MA. Plan to get an early start so you have enough time to enjoy Nantucket. Make sure to make a reservation ahead as the Fast Ferry fills up quickly in the summer. You won’t need your car as almost everything that you’ll want to see and do will be easily accessible on foot. These are the top things to see in Nantucket:
  • Whaling Museum – Once the whaling capital of the world, Nantucket’s Whaling Museum offers a glimpse of it’s famous past and the industry that paid for all of the charming gray-shingled colonial houses you will see on the island.
  • Bike Rentals – After getting a little history lesson at the museum, rent a bike and explore the island. There are tons of bike rental shops to choose from and biking on this island is extremely easy (except for the cobblestone streets of downtown) as it’s a very flat island for the most part.
  • Brant Point Lighthouse – Ride or walk over to this lighthouse near the harbor. The second-oldest lighthouse in the U.S., it’s a cute smaller lighthouse (as opposed to a giant like the Cape Hatteras Lighthouse) and worth a look-see.
If you have extra time after your day in Nantucket, drive out further on the Cape to Provincetown for another day trip. It’s a great place to visit – plenty to see, lots of great restaurants, shops, and bars, and the nearby dunes have to be seen to be believed, they are so huge.

East Coast Road Trip – Stop 4
Lake Sunapee, Newbury, New Hampshire
Suggested Number of Days: Two Days
For a change of pace from the ocean, check out this beautiful lake – the highest large lake in America (1100 feet above sea level). This year-round destination offers every type of outdoor activity and offers a classic summer lake getaway experience.

  • Sunapee Express Chairlift – Take this chairlift (usually for skiers in the winter) up the mountain for breathtaking views of the mountain and valley. If you want to take a hike, you can get off at the top and hike down.
  • Kayak or Canoe Rentals at Sunapee Sports – Rent kayaks or canoes and explore the lake from Sunapee Harbor. This is a great way to really get a feel for the lake.
  • Mount Sunapee State Beach – Take a swim and have a picnic at this beach. You’ll have wonderful views of the lake and the surrounding mountains.
East Coast Road Trip – Stop 5
Maine
Suggested Number of Days: Three to Four Days
Maine is beautiful at this time of year and a refreshing change from the sweltering heat of the summer elsewhere. You will find that it will be too cool to wear shorts and t-shirts unless it’s the middle of a sunny day, so make sure to pack a jacket, long pants, and some sweaters.

My favorite thing about Maine is the wonderful seafood. You will find little shacks all along the coast selling bowls of steamers and lobster rolls at very affordable prices. There’s nothing like sitting in a picturesque harbor or on a deck near the crashing waves of the ocean and eating seafood that was caught that morning. Delicious! Check out this Maine road food article for specific suggestions.

Besides eating seafood, what else should you do as your East Coast road trip continues through Maine?

  • Acadia National Park – You can see this beautiful park from your car, driving the Park Loop Road, or get out and explore the miles of hiking trails. The trails that run along the coast are my favorite for seeing whales right from the shore, which will be migrating through this area July through August.
  • Outlet Heaven, Freeport, Maine – If you love to shop, you’ll think you’ve died and gone to heaven. Practically every major clothing company has an outlet or factory store here with lots of great deals. A must-see if you’re not much of a shopper is the L.L. Bean store. With its huge Bean Boot that stands out front, boot-testing boulder-climb, Ben and Jerry’s ice cream shop, giant stuffed moose, travel agency, and stocked trout pond, it’s more than a store – it’s an experience!
  • Lighthouse Trail – The lighthouses of Maine are a sight to behold on their craggy outcroppings that look like something straight out of a painting. In fact, they have been the subjects of many famous paintings, so the impression you’re in a painting isn’t far off. At the very least, see the Portland Head Light with its museum and cliff walk that runs along the shore offering spectacular views of Maine’s rocky coast.
With this east coast road trip, you’ve gotten a chance to sample every great summer activity and sight that New England has to offer. If you have extra time on your return trip, stop in Boston and take in the sights of this historic city.

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