Portland Head Lighthouse is a must-see on your roadtrip

Boston to Portland Maine: The 2023 Trip Guide (By Car or by Train!)

Boston to Portland Maine is one of the best small road trips in the U.S. While the cities are less than two hours apart, you can extend the trip to include many scenic charming towns and coastal views along the way. If you enjoy lighthouses, beaches, and fresh seafood, this is the perfect road trip itinerary for you!

Driving from Boston to Portland

The drive from Boston Massachusetts to Portland Maine itself is pretty straightforward and can take about 2 hours (110 miles) direct on I-95. However, you may want to stretch the journey out to a few more hours or even a few days to see what the New England coastline has to offer. I’d suggest taking a weekend to explore the scenic route, but even an extra few hours can be worth it to take some detours.

Scenic stops on the way from Boston to Portland

If you fancy exploring the coastline or taking a scenic route be sure to incorporate some of these stops into your drive. Leave plenty of time for exploring!

Boston Public Gardens


It goes without saying, but be sure to spend a day or two in Boston before you head north. Take a historic walking tour on the Freedom Trail, watch a RedSox game at iconic Fenway Park, or stroll in the park at Boston Public Gardens. The Waterfront also offers scenic views of Boston’s skyline as well as ample opportunities to grab a lobster roll!

You could easily spend 3 days in Boston so be sure to make it a stop on your drive up. Fly directly into Logan International Airport to begin your road trip.

Salem, Massachusetts ~35 minutes from Boston

Salem is the first recommended stop on the road trip due to its historic significance in the Salem Witch Trails. In 1692 25 people were killed for accusations of witchcraft in Salem.

I’d recommend visiting the Salem Witch Trial Memorial as well as the Old Burying Point Cemetary. Stroll down the pedestrian friendly Essex street and stop by the quirky monster and magic-themed shops along the way. This town takes witchcraft seriously.

Be sure to take a Hocus Pocus tour to see some of the houses from the films, as well as a ghost tour to hear about the spirits that still haunt Salem. In October Salem becomes a tourist destination for all things spooky!

Visit Salem's Witch Trial memorial

Newburyport ~40 minutes from Salem

Newburyport would be a perfect stop for an hour or so to stretch your legs and grab a coffee. It is a quaint town with a beautiful waterfront and cute boutique shops. Check out the Market Square!

If you are interested in exploring the Parker River Natural Wildlife Refuge you could easily spend a full day here. The Wildlife Refuge is on Plum Island and has over 3000 protected acres of salt marsh.

Head straight to the beach, or peruse the biking and walking paths that are perfect for birdwatching. For a quick and easy boardwalk trail, stroll along the Hellcat Interpretative Trail which is an elevated boardwalk through the marshes and dunes. 

If you are looking for a quirky landmark on Plum Island, visit the “Pink House”, an abandoned house built as a result of an ugly divorce in the early 1900s. The ex-wife desired to live in a copy of their formal home in Newburyport and the ex-husband agreed to build it for her- but put it in the middle of nowhere out of animosity!

  • Travel Tip: If you want to extend the itinerary further, there are countless quaint fishing towns worth exploring along Massachusetts’ north shore. Explore Marblehead, Manchester by the Sea, Gloucester, Rockport or Essex or go on a whale watch and eat a lobster roll!
Plum Island has salt marshes and dunes

Hampton Beach & Portsmouth, NH ~30 Minutes from Newburyport

New Hampshire is famous for its skiing, and fall foliage but also its gorgeous (although short) coastline. New Hampshire has 30 miles of coast between Massachusetts and Maine that offer quaint towns as well as lively beach activities.

Crossing into New Hampshire, I’d recommend first stopping by Hampton Beach State Park. This beach is very crowded during the summer as it’s a popular spot for families. It has nightly live music, weekly fireworks as well as the sand castle competitions and talent contests. You could easily spend an entire day here on the sandy coastline or you could stay in the RV park. Advance reservations required.

If you’ve had enough sun for the day, head up to Portsmouth New Hampshire. Portsmouth is a cute charming town with plenty of local shops and restaurants. Grab a bite to eat or stop in for a beer at a local pub.

Ogunquit Maine is a charming fishing town

Ogunquit, ME ~ 30 minutes from Portsmouth

Ogunquit Maine could be a perfect final destination if you don’t want to travel up the final 45 minutes to Portland. This quaint town of only 4 miles has spectacular ocean views as well as a charming town center. 

For a quick stop, I’d suggest taking the Marginal Way to Perkins Cove which is a mile long (each way) pathway along the coast. Stretch your legs and enjoy some beautiful vistas. If you plan on staying longer there are countless beach activities to enjoy such as sailing, fishing, or beachcombing.

The town center is also worth a visit! Stop by the Ogunquit Museum of American Art as well as countless galleries and boutiques.

  • Travel Tip: Have additional time? Halfway between Portland and Boston is York/ Cape Neddick, Maine. Worth a stop to grab a coffee and check out the lighthouse!
Kennebunkport Maine is a cute stop on your road trip.

Kennebunkport ~30 minutes from Ogunquit

The next stop on your Boston to Portland road trip should be Kennebunkport, one of the oldest towns in the U.S founded in the early 1600s. It has a coastal quaint atmosphere with the Kennebunk Port river running through town along its waterfront. 

I’d suggest stopping by Colony Beach as you can view boats coming into the town harbor. Stroll through the town center where you will find plenty of local art and shopping. Try some of the local fresh seafood- fancy another lobster roll?

If you have some additional time, I’d recommend exploring the ocean and taking advantage of the sailing, whale watching, and many other activities in Kennebunkport.

Old Orchard Beach ~30 minutes from Kennebunkport 

The pier at Old Orchard Beach is a must-see stop! The old-fashioned carnival-like pier sells street snacks like fried dough and cotton candy. Walk on the beach below for some cool views of the shops along the pier. 

Explore the town for more great food and shops. Keep the party going as there is mini-golf and carnival rides near downtown.

  • Travel Tip: Parking will be fairly expensive ($20) close to the pier and charges per day (not per hour). This price may discourage visitors only looking to stay a few hours.
The pier at Old Orchard beach is a must see for its old-fashioned carnival feel

Cape Elizabeth, ME ~30 minutes from Old Orchard

While technically in Portland, Cape Elizabeth Maine is a perfect stop to see some quintessential New England lighthouses. There are three main lighthouses- Portland Head Light, Spring Point Ledge Lighthouse, and Bug Light. The lighthouses are pretty close together and shouldn’t take more than an hour or two to visit. If you only have time for one lighthouse visit the Portland Head Light, one of the most iconic landmarks in Maine.

Portland ~15 minutes from Cape Elizabeth

Once you finish your road trip to Portland you should definitely spend a day or two in Portland. Portland is absolutely worth a visit as the downtown is walkable and there is plenty to see.

Known for its thriving food and drink scene, you should tour the local breweries (try famous local brewery Allagash) or explore the seashore by taking a ferry to Peaks Island. Farther out from downtown, you will need a car to explore greater Portland. Eat all the food you can in Portland!

There is plenty more to explore in the Portland area from local beaches in Scarborough to the L.L. Bean flagship store in Freeport.  

The portland area has several light houses

What is the best time of year to visit Portland, Maine?

There really is no right time of year to do a Boston to Portland road trip! Crowds flock to coastal New England cities in the summer so expect busy traffic during the high season. In the summertime all the seasonal businesses- ice cream, snack shacks, beach restaurants, etc- would be open. After labor day in September, the seasonal tourist shops/businesses will close down and the towns may seem a bit quieter.

If you are looking to avoid crowds, spring or fall would be a beautiful time to stroll through charming towns or along the beach. The winter is also pretty but that coastal wind chill may dissuade you. Many beaches will allow dogs off-season so you could bring your canine friend. 

Downtown Portland Maine

Getting to Portland from Boston without a car

There are a few options to get to Portland without a car including the Amtrak Downeaster or regional buses. Both options take about 2 hours, only slightly longer than driving. Perfect for a day trip or long weekend!

Amtrak to Portland

The Amtrak Downeaster takes 5 daily roundtrips from Boston’s North Station to Brunswick, Maine starting at 8:30 am. The trip via Amtrak takes about 2.5 hours with several stops along the way.

Train fares vary by destination but cost anything from $3-30 depending on the level of the ticket. Reservations are required before boarding. Bikes and small pets, with pre-booking and a fee, are allowed to board which means you could plan to bike around Portland!

There are lots of discounts for Downeaster tickets including 50% discounts for children and 65-plus seniors as well as medical care, veteran, and student discounts. Check before you book because there are often flash sales such as buy one get one half off, and group/family discounts.

Book ahead of time and maximize deals, and the Amtrak train can easily be the cheapest way to get to Portland from Boston.

Amtrack map from Boston to Portland

Roadtrip via Train

You are still able to make a “road trip” out of the Amtrak ride to Portland. One of the first several stops would be in Durham, New Hampshire. There is a free shuttle (run by a nearby university) that takes people to Portsmouth. Portsmouth would be a perfect road trip stop for those who want to spend some time on the beach or taste some of the local seafood.

Another “road trip” option would be taking the train further to Old Orchard Beach for a day of swimming and laying on the beach.

Bus: Greyhound and Concord Coachlines

Another affordable way to get to Portland without a car is the Greyhound or Concord Coachlines bus. Tickets start at just $15 one way from South Station in Boston. Concord Coachlines, a regional interstate bus system, also offers direct service to Portland from Boston’s Logan airport.

The bus will not have the amenities- free wifi, and for-purchase snacks- that the Amtrak will have but may be a bit faster since there are no stops in between.

If you want to take the train right to Portland you will get dropped off in the downtown area near great restaurants and attractions. 

Boston to Portland Ferry

There is no ferry from Boston to Portland. But once in Portland, there are ferry options to Bar Harbor, ME or Canada.

Coastal Maine is a must-visit trip

In Conclusion: Boston to Portland

Boston Mass to Portland Maine can easily be done in a day but better to set aside a weekend to explore. Drive up and turn the journey into a road trip stopping at coastal towns in Massachusetts, New Hampshire and Maine. Dont have a car? Take the Downeaster Amtrack to Portland and explore restaurants and shops downtown.

There is plenty to do along the New England coast from visiting beaches, fishing, kayaking and seeing historic lighthouses. Visit the shops in charming towns and enjoy the quaint sealife atmosphere. And prepare yourself for some of the freshest seafood you’ve ever had. The lobster is an absolute must as its harvested right off shore!

You could even take the road trip a step farther and go north to Acadia National Park or Bar Harbor. Maine has so many destinations to offer visitors but a Portland road trip is a must!