We personally think September is one of the most underrated times to travel during the year.

The crowds have finally started to die down from the crazy busy summer months, yet you can still take advantage of long days and warmer temps. 

Of all the places you could choose to dedicate those lazy, hazy, crazy last days of summer, we’re personally rooting for New England.

Whether you’re looking to immerse yourself in some culture, enjoy a picturesque beach day in a charming seaside town, or something more adventurous like watching the sunrise over a mountaintop, it truly is impossible to run out of things to do.

1. The first place to check out on our list is the swoon-worthy Martha's Vineyard

With six different towns to visit on the island, you can spend days here and still never run out of things to do. 

Once you land in Oaks Bluff, you must grab a mudslide from Donovan’s Reef. It’ll be well worth the line.

We’d suggest renting a bike (if you’re into that kind of thing) and heading over to Edgartown for the afternoon. It’s an easy, breezy coastal ride, and you’ll quickly be swept away by the ocean views and hydrangea-filled streets. On your ride into downtown Edgartown, you can stop by the famous Jaws bridge and if you’re up for it, take the plunge. We swear it’s higher than it looks. 

After you’ve spent the afternoon learning about the history behind the island and filled up on all the seafood the vineyard has to offer, we think it’ll be well worth your time making the trek over to Menemsha. While you’re looking at about a 45-minute drive, the world-famous sunsets in this magical little fishing village are well worth it.

2. Portland, Maine

Maine - The way life should be.

Portland is the epitome of New England summer. After about a two-hour drive from Boston, you’ll find this scenic waterfront city in the southern part of Maine.

Filled with beaches, fishing charters, hiking trails, art galleries, and beautiful historic homes, we promise there’s something for everyone. 

We suggest spending an afternoon in Old Port strolling along the cobblestone streets and sampling some of the fantastic restaurants this foodie city has to offer. Quaint Old Port, while filled to the brim with a rich history, is also incredibly trendy. The options are endless, from lobster grilled cheeses on the waterfront to omakase in a fancy Japanese restaurant to pub food at one of the many local watering holes.

Looking to get out on the water while in town? Be sure to check out Portland Schooner Co’s two-hour sailing trips on Casco Bay and let the sun and salty air soothe you for an afternoon. 

Last but not least, it would be remiss to visit Portland and not check out one of their many craft breweries; we vote for Allagash Brewery or Bissell Brothers, but you really can’t go wrong with wherever your taste buds lead you.

3. Bar Harbor, Maine

It’s often said that nothing worth having comes easy, and that’s exactly the case when it comes to the next stop on our list, Bar Harbor, Maine. After you make the three-and-a-half-hour drive from Portland, you will quickly be rewarded with the jaw-dropping views in Bar Harbor. 

For a small town, it makes up for it with plenty of bars, restaurants, and places to stay, all within walking distance from one another. You’ll feel like you’ve gone back in time to the simpler days as you can spending hours wandering through the streets and enjoying the authentic vibes of this summer town.

You can’t visit Bar Harbor and not spend time checking out the stunning Acadia National Park. There are plenty of beautiful hiking trails to check out, ranging from easy to difficult, making it perfect for everyone to enjoy. On a warm afternoon, be sure to check out Sand Beach or Jordan Park for some relaxation. 

If you’re up for a (very) early wakeup, the sunrise from Cadillac Mountain is, without a doubt, a sight to see. In addition, you’ll be front row to a mountaintop view of downtown Bar Harbor.

4. Newport, Rhode Island

Last but not least on our list is Newport, Rhode Island.

There is genuinely nothing Newport doesn’t have. Not only is it home to some of the area's most beautiful waterfront mansions (think Great Gatsby), but the restaurant and summer nightlife scene is prime time. Think live music, colorful seafood dishes, and an array of waterfront spots that will make all of your Instagram dreams come true.

We highly suggest grabbing a cup of coffee and getting your steps in while walking along the cliff walk. The ocean views alone are worth it, not to mention the stunning architecture and historical homes you’ll be privy to along the way. 

After you’ve had as much lobster and clam chowder as your heart desires, head over to one of Newport’s beautiful beaches for a relaxing afternoon in the Rhode Island sun. 

We suggest ending your trip with a visit to Newport Vineyards. Here you can sip on some local wine while looking out at the property's beautiful landscape. 

We know we’ve left you with a tough decision of where to head this September. Luckily, we’re extremely confident you’ll be happy with whichever coastal spot you choose.


Discover the charm of New England's coastal towns in September, a hidden gem of travel timing. As summer's hustle subsides and pleasant weather prevails, seize the opportunity for cultural immersion, beachfront bliss, and adventurous escapades. Embrace the essence of September in New England for a diverse range of unforgettable experiences.