Looking for a quick weekend getaway? We’ll cover some popular & hidden gems in this article on the Northeast. My preferred time here is always in the summer, but fall foliage cannot be missed and spring is lovely as well. The winters are COLD so use this for some daydreaming or future planning! Mini-moons, honeymoons, baby-moons, anniversaries are all popular at these locations. I’ll cover NYC separately as it’s near and dear to my heart having lived there for 5 years and experiencing just the best time of my life, alongside meeting my husband and incredible besties. Let’s dive into some of the top hidden gems to beat the tourist crowds and get a local experience of the beautiful North East Tri states & New England. Trips by Nic absolutely adores some of the popular places like Nantucket, Martha’s Vineyard, The Hamptons, Block Island, Lake Winnipesaukee and others but this roundup today is to focus on some smaller, less popular destinations that might just fill your cup for that northeast getaway feel. 

Newburyport, MA & Plum Island

While I am biased having grown up here, it is a quintessential New England town. Beaches, boats and a cobblestone street downtown lined with shops and restaurants with local seafood. Everything you could want in a weekend getaway, especially in the summertime! Though I would avoid the last week in July and first week in August, each year this is the annual ‘Yankee Homecoming’ celebration. While you’ll get tons of activities, and live concerts on the waterfront each evening, you’ll also get swarms of crowds. It is fun though as some larger boats come into port for the occasion (you’ve been warned)! PS it’s a great spot for a wedding, I may or may not have gotten married here….though the original one was planned for Shelter Island, read on to cover that picture perfect NY island near the Hamptons.


Where to stay: Blue Inn on the Beach

True hidden gems blend in and you don’t even realize how luxurious it feels until you’re here. Pool, directly on the beach front, bikes to take around the adorable tiny island, all at your footsteps. I can’t get enough of this tiny little 5 star inn. You can take a car into nearby Newburyport if you want to try additional restaurants and bars off of Plum Island. We recommend The Tuscan Grill for oysters or Agave for a Margarita.
What’s super comparable to Newburyport just down the road and in nearby New Hampshire? Portsmouth,NH, slightly larger than what you’ll find in Newburyport, we like this for a wider array of restaurant, bars and shopping availability and more direct waterfront  dining options with views.

Shelter Island, NY

Skip the Hamptons and head straight for Shelter Island. I promise it won’t disappoint. You’ll avoid the mayhem and crowds in East Hampton and Montauk but you’ll get good beaches, sunsets, tons of water views and even some fantastic restaurant options by renowned chefs. You need to board a boat to get here, there are no bridges or other ways to arrive than via the North or South Ferry. Trips By Nic highly suggests you drive out to Greenport, via the train from NYC or the Hampton Jitney (North Fork route) and then hop on the North Ferry to Shelter Island Heights. This is the road less traveled. Though you’ll seem some sneaky Hampton goers driving out to Greenport and cutting through SI to get the Sag Harbor. Okay enough about that. What is there to see and do on this quiet, quaint and adorable island!! 

In addition to laying at the beach or taking a boat out for the day, I always like to bike around the island. Rent a beach cruiser and go look for some wildlife or tour the stunning, large mansions in Dering Harbor. I also love to walk over to the North Ferry and then grab dinner or drinks in Greenport. Claudio’s is a fun scene, people arriving on their boats to listen to the live band. Alternatively, if you take the ferry over on the South Side to Sag Harbor on the Hamptons side, you’ll want to take a car for this but you can go shopping for the day then sneak back to your hideaway on Shelter. We sometimes take a drive out to Montauk, End of The World as well. I’ll cover Montauk as a brief highlight, it’s certainly no hidden gem anymore but it’s fun nonetheless.

Sunset Beach

The French Riviera isn’t so far away when you’re at Sunset Beach. This is modeled after the endless beach clubs you’d find in Cannes and Nice but right here in good old NY. Sip an Aperol Spritz on one of the trendy decks while watching the most amazing sunset. Or play ping pong in the back and gather your friends at a table for bottle service while partying it up. You can also lounge on the beach right out front. Stay here if you want the ultimate French Riviera experience. 

Vine Street Cafe: this is a top notch restaurant that you’ll see people coming over from the Hamptons to eat at.

The world is your oyster!

Portland, ME

It goes without saying that this is already popular and frequented by many tourists. From bachelorette parties to mini-moons, it’s certainly a staple in New England. You can easily grab a direct flight from many airports around the country into Portland, and be eating a lobster roll within 10 minutes. Eventide has the best oyster shooters ever and delicious seafood all around.


Norway, ME and Lake Pennesseewassee

Stay: The Woods, ME

Could there be a more picturesque hideaway? We think not. Downtown Norway has the most quintessential Maine shop, restaurants and even Norway Brewing company to sample some delicious local beers. It is definitely off the beaten path for most known Maine destinations such as York, Portland, Old Orchard Beach and Ogunquit.

The lake has a boat-friendly Lake Store (literally called, The Lake Store) that you can dock your boat off and grab some freshly made donuts, or pies. There is a locals joint called Boomers that you also can boat to for a quick drink. We like this lake because it is not crowded with tourists in the summer. It is cozy in the winter and tucked away on hidden roads in the woods. You can waterski, tube, paddleboard, kayak and more here. There are several nearby hikes as well if that floats your boat more than actual boating.


Wrapping this up with some popular places you may have heard of that we certainly do recommend and book for, they are a bit more mainstream but absolutely worth the visit anyway! Trips by Nic can help you book any of the above or below to fit your needs 🙂 The Cliff House in Maine, Cape Cod, Nantucket – specifically at the Wauwinet and Gurney’s in Montauk! Let us know where you go in the north east and how you like it! These are especially good options if you’re not up for international travel yet during this global pandemic we are still in.