- Take a road trip through captivating cities in the Northeast, with scenic natural wonders and cozy towns along the way.
- Explore charming villages and coastal hubs like Kings Point and Mamaroneck, New York, and enjoy breathtaking views and fun activities.
- Visit historic cities like Bridgeport, Connecticut, and Narragansett, Rhode Island, before reaching Manchester-by-the-Sea, Massachusetts, and Rye, New Hampshire. Finally, experience the charm of Kittery, Maine, and its neighboring town, York, and end the trip in South Portland, Belfast, and Machiasport, Maine.
Envision a journey through captivating cities in the Northeast, accompanied by cherished friends and family or even embarked upon solo. Feel the exhilarating breeze tousling your hair as you cruise along I-95, bound for Maine, with a palpable sense of adventure in tow. Starting in New York City, there are neighborhoods where one can sightsee for less than $50 a day, and crossing through New York state, individuals can find small towns near scenic natural wonders.
After parting from New York state, the road trip will take travelers along the Northeast coast, with the next stop being the beloved Connecticut. Fall in love with the state and the many things to do in Mystic, Connecticut’s favorite small town, before stopping in Rhode Island and enjoying the many cozy towns that will make anyone consider retirement. Next, explore the second-largest city and the perfect alternative to Boston in Massachusetts or scenic day trips that one can take through snow-covered mountains in New Hampshire before stopping on the final leg of the road trip, the magnificent Maine.
The length of the road trip is roughly 8 hours and 54 minutes driving one way.
10 Kings Point, New York
Start the first leg of the trip near the Big Apple before hitting the great outdoors
Kings Point Road in the incorporated Village of Kings Point, New York
Kings Point, New York, is a quaint village in North Hempstead in greater Nassau County. Its name commemorates the late Governor John Alsop King, who inherited the land in the mid-1800s; however, it was later incorporated into North Hempstead in 1924. It earned its charm and is renowned today for its role in the Roaring 20s due to the illustrious festivities the town’s residents hosted during that time.
9 Mamaroneck, New York
Known for its community vibe and breathtaking views
View of the Mamaroneck Harbor in Mamaroneck, New York
The town of Mamaroneck, New York, is a beautiful coastal hub with astonishing scenery and fun activities suitable for all ages. Officially established in 1788, the area became recognized for its pervasive agriculture, food, lumber, and milling industries. Now, it’s a beautiful place to relax, have fun, and enjoy the various cuisines on this once-in-a-lifetime road trip.
When driving across the New York state line, be sure to have cash on hand for the tolls or have an EZ Pass ready. Moreover, be prepared for the impending traffic!
8 Bridgeport, Connecticut
Visit the fifth-most populous city in Connecticut on the next stop of this grand adventure
Front view of St. Augustine Cathedral in Bridgeport, Connecticut
Parting from the grand New York state, Bridgeport, Connecticut, is the next stop on the journey. Situated in Fairfield County and first colonized in the mid-17th century, Bridgeport is a city filled with history and landmarks. It was officially incorporated in 1821 as a town and gained its title as a city in 1836. Now, it is recognized as the fifth most populated area in Connecticut.
7 Narragansett, Rhode Island
Take a dip on the next stop of this trip
Panoramic view of the waves at Narragansett, Rhode Island
Narragansett, Rhode Island, was first settled by the Narragansett Native Americans, who existed there for centuries before the first settlers set foot on the land. It eventually transformed into a colonial city in the 17th and 18th centuries. Today, Narragansett is a relaxing seaside location that accommodates the resort industry and individuals looking to relax on the Northeast’s beautiful beaches.
6 Manchester-by-the-Sea, Massachusetts
Sightsee in this magnificent town
View of Eaglehead in Manchester-by-the-sea, Massachusetts
Not too far from the Boston city center and right next to the ocean, Manchester-by-the-Sea, Massachusetts, is the perfect place to be. The town is located in a region known as the North Shore and roughly 30 minutes from the famous Boston city, as mentioned on the town’s website. The Great and General Court of the Commonwealth incorporated the city in 1645, and since then, it has grown into the lovable seaside haven it is known as today.
5 Rye, New Hampshire
Explore the longest coastline in New Hampshire!
View of Jenness Beach in Rye, New Hampshire
The following stop on this road trip is the renowned Rye, New Hampshire, known for having the longest coastline in New Hampshire, eight miles to be exact. First inhabited by Native Americans, traces of their legacy remain in the city. However, it was eventually colonized and became a European settlement in 1623. By 1785, Rye, New Hampshire, had official township status and slowly transformed into the beach city it is today. Travelers can find brilliant beaches, exciting coastal activities, and beautiful marshes, salty and fresh.
4 Kittery, Maine
Understand why Kittery is known as “Maine’s First Town,” according to the town’s website
Crewmembers aboard the Coast Guard Cutter Tahoma in Kittery, Maine
Kittery, Maine, also recognized as Maine’s oldest town on its website, is a charming port town with an extensive history dating back centuries. Initially owned by the Amiciskeag Native Americans, the land has cultural ties to fishing, for the tribe’s name translates to “fishing point.” The first Europeans occupied the land in 1623 and had amicable relations with the Natives who resided there at first. After years of development, the town became home to the country’s oldest active Navy yard and even helped create Navy submarines during WWII.
When in Kittery, Maine, make sure to stop by its neighboring town, York, Maine, for twice the fun!
3 South Portland, Maine
Enjoy the 4th largest municipality in Maine, according to the town’s website
Docks in Ferry Village in South Portland, Maine
South Portland, Maine, is a beautiful seaside escape and the next destination on this adventure. Located within Cumberland County on the Southern Maine coast, the city was occupied in 1630, and it eventually became incorporated as a town in 1895. Now, the community is home to roughly 27,000 residents and is the fourth-largest municipality in Maine. In this beautiful town, travelers can find many activities, natural beauties, and welcoming residents.
2 Belfast, Maine
Fall in love with the community in Belfast, Maine
View of Main Street in Belfast, Maine
Community and culture permeate Belfast, Maine, from its local restaurants and bakeries to the town’s downtown area. Native Americans lived in the area before the first European settlements, specifically Scottish-Irish families, arrived in 1770. According to the town website and urban legend, the town’s name was derived from a coin toss. The toss settled the dispute, and the city became known as Belfast. The town was later abandoned for fear of British retribution, but the Scottish-Irish colonizers eventually returned in the 1780s, establishing the seeds for its current development. A Northeast road trip would be incomplete without exploring this city, drenched in rich culture and fostering a close-knit community that might captivate and charm travelers.
1 Machiasport, Maine
See what makes Machiasport, Maine, so magnificent on the last stop of this road trip
Fort O’Brien (also known as Fort Machias) in Machiasport, Maine
The final destination on this trip of a lifetime is the immaculate Machiasport, Maine. The town, adorned with a rich history and the architecture to match it, is nothing less than gorgeous. First home to Native Americans, it was settled in 1763 by European colonizers and officially incorporated as a town in 1826. Visitors can appreciate the various relics from the past while enjoying the neighboring shoreline and recreational activities.