The drive from Boston to Portland, Maine, is one of my favorites in New England. There are so many quaint, charming coastal towns and beaches to stop at along what I’d consider a short drive (2 hours) to choose from! We’ll get into my favorites in this post.
I spent time living in Boston during college and got to explore so much of New England. The area between Boston and Portland is one of my favorite US road trips because it is so scenic, with tons of different options for things to see and do. You’ll love this drive and the chance to explore both Boston and Portland on a trip.
All stops are listed as closest to furthest from Boston.
Table of Contents
Logistics to Consider
Before we get into the drive, let’s cover some of the most important logistics and things to figure out before you start your drive! Below are some top FAQ about driving from Boston to Portland.
Tips for Driving in New England
In general, driving in New England is pretty easy! As someone who grew up in Texas, I found the driving around Boston challenging at first. People do use their horns here more often, and they are more aggressive than I was used to!
You’ll also need to be ready for a toll road with different pay stations between Boston and Portland, and plenty of roundabouts!
None of these things is too much to handle; you’ll be fine, but it’s good to know about them before your drive.
Public Transit Options
If you don’t want to drive, you’ll find that most of the towns on this list will still be accessible! You can easily use public transit to get from Boston to Portland and back, and you can stop at different places along the way.
There are two main public transit options to know about, and they are essential to distinguish: one does not go all the way to Portland, but can make day trips from Boston possible.
- MBTA or the T, as locals call it! This is the Boston area transit system and commuter rail that will take you to many places around Boston, even an hour or more away from the city.
- Amtrak: Is the national passenger railroad corporation of the United States, a federally supported company that operates most of the country’s intercity rail passenger service. The available stops in New England are fairly extensive compared to other parts of the US.
There’s also a crossover between MBTA and Amtrak stops. I’ll note those at the very end of each section for each town on the list.
How Long is the Drive from Boston to Portland?
The drive from Boston to Portland without traffic is about 1 and 45 minutes. However, depending on the time of day you leave Boston, this can be much, much longer.
Avoid leaving Boston during rush hour on a weekday for the shortest driving time. We left on a Saturday morning around 8:30 am and hit zero traffic!
You’ll also find that the stops I share aren’t necessarily right off the highway, so you can expect this drive to take you more like 4-5 hours if you make all the stops (impossible in one day to do it all, obviously). You could consider stopping midway in one of the towns, or hit half the stops one day and half the next if you want to visit more!
Each of these stops could also be extended to a full day or weekend if you wanted. Meaning, this could be a short trip or a long one – totally up to you! I’d recommend having at least 4 days to make the most of this trip—more on a suggested itinerary below.
Best time of year to drive from Boston to Portland
New England is a year-round destination, and as someone who has explored the area in all seasons, I can say that I personally love them all. You can certainly make the case for visiting any time of year!
However, I think this particular drive is best suited for April through October, with the best times being late May and early September. These are the times when the weather will be nice, there are fewer crowds, and you’ll get the most out of coastal New England life!
Fall in this area is also really beautiful, but if I had to choose between coastal New England and the mountains of New England in the fall, I’d opt for New Hampshire and Vermont in the fall, and for this Boston to Portland drive in the summer.
Visiting in winter means quiet towns, fewer tourists, and a local experience. It also means that many things will be closed or on reduced hours, so we will take some additional planning to make stops between the two major cities happen!
Spring in New England can be cold and wet, but it can also be enjoyable, with lots of pretty flowers! I would say Spring has the least predictable weather of any season, so it’s definitely a possible time to visit, but it could also end with rain or sunny weather throughout the trip.
Suggested Itinerary
Below is a quick overview of a suggested itinerary I have for you! However, this guide will go over each of the stops between to consider in more detail, so you can easily swap them in or out based on what you want to do most. Use this suggested itinerary, or just the list of stops below, to make your own amazing Boston to Portland, Maine road trip.
- Day 1: Explore Boston
- Day 2: Salem, MA and Kennebunkport, ME
- Day 3: Portland, ME and Cape Elizabeth, ME
- Day 4: Portsmouth, NH, and Rockport, MA
If you have more time or are visiting in the summer, add a beach day in a town like Old Orchard Beach or Ipswich, MA.
Stop 1: Salem, MA
Salem is known for the Salem Witch Trials and can get extremely crowded during the fall, but it’s great to explore no matter the season! Downtown Salem is really charming, with a harbor and many unique shops to explore.
I’ll be the first to admit that Salem is one of those towns that feels pretty touristy to me, but if you’ve never been before, it’s well worth going to!
While here, make sure you:
- Visit one of the museums about the history of Salem, like the Salem Witch Museum, the House of Seven Gables, or the Witch House. Stop by the Bewitched Statue
- Grab some unique souvenirs in the shops on Essex Street.
Pro tip: If you visit in the fall, expect to struggle to find parking here. Salem is one of the most famous places to visit on Halloween. Be very careful of street parking, as there are many rules to save the parking spaces for locals (as they should!).
Accessible on the T from Boston, 35 minute drive
Image by Anne and Saturnino Miranda from Pixabay
Stop 2: Rockport, MA
Rockport is a bit out of the way on this drive, but I think it’s well worth a stop. The first time I visited Rockport, I remember having the best clam chowder of my life at the port and just taking in the calm as the sun began to set (I wish I remembered where, but that was 15 years ago!).
Downtown Rockport is probably one of the most iconic coastal New England towns, famous for Motif #1 – a red fishing shack, located in Dock Square. It is one of the most painted and photographed structures in the world. As you can imagine, just walking this town can warm your heart!
While in Rockport, don’t miss:
- Exploring some of the 30+ art galleries in town
- Visiting the harbor for amazing lobster or clam chowder
- Relaxing on the beach, consider Long Beach, Cape Hedge Beach, and Front Beach
Accessible on the T from Boston, 1 hour drive
Stop 3: Ipswich, MA
Our next stop after Rockport is Ipswich, MA. This cute seaside town is along the north shore of Massachusetts. The drive between Rockport and Ipswich is a beautiful coastal drive you’ll love!
Ipswich is a great stop for those who want to explore the outdoors and history. You’ll find beautiful coastal views here, and while it has a cute, historic downtown, my favorite things to do are on the outskirts!
While here, make sure you:
- Visit Crane Estate and explore the views from Castle Hill; there’s also a great beach here
- Hike or canoe along the river or explore the marshes
- Visit a historic working farm like Appleton or Russell Orchard
- Explore historic homes and walk through the downtown area
Stop 4: Newburyport, MA
The last stop before we head into a new state on this list is Newburyport. Newburyport is a charming coastal town with a small-town feel and plenty of things to do.
This is an excellent stop for all different types of travelers. If you want some history and great boutique shopping, you’ll love it here. If you want a lovely beach and coastal activities, again, you’ll love it here!
This is a stop you could easily spend an entire weekend at, but if you only have a few hours, it’s still worth a stop. I’m sad I didn’t get to revisit on my last trip, as I love this charming town.
Things you don’t miss in Newburyport:
- Rent bikes from Port Bikes or electric bikes from EZ Pedlar and enjoy a ride along the coast or on the Clipper City Rail Trail
- Visit Plum Island for some beach time
- Shop in Tannery Historic Marketplace, a hub of independent shops and boutiques
Accessible on the T or Amtrak from Boston, 46 minute drive
Stop 5: Portsmouth, NH
One of the bigger towns on this list with tons to do is Portsmouth, NH. I’ve visited a few times and feel there’s still more I could do here. Portsmouth is a great stop for history lovers who want to learn more about New England while in a charming coastal town.
There are a lot of history museums here, and great things for families to do here. Plus, amazing food! You could easily spend a weekend here just exploring. On my latest trip, we stopped for a half-day and felt we could have spent much longer.
Here are a few top things to do in Portsmouth, NH:
- Explore history at the Strawberry Banke Museum
- Shop around in Market Square, where you’ll find plenty of boutiques, shops, and restaurants with historic charm
- See the one and only mainland lighthouse in New Hampshire – Portsmouth Harbour Lighthouse. You can take a bike tour along the coast or a harbour cruise for great views.
Accessible on the Amtrak from Boston + bus, 1 hour 10 min drive
Stop 6: Kittery, ME
Known as the oldest incorporated town in Maine, Kittery has plenty of historic charm, but visiting this small town goes beyond that! Kittery boasts a rich maritime history, historic homes in areas like Kittery Point, and beautiful beaches, making it a great place to spend extra time relaxing in the summer.
Don’t miss these highlights in Kittery:
- Explore the charming downtown area of Kittery Foreside for an authentic small town Maine atmosphere, with a variety of chef driven restaurants, local coffee shops, and boutiques.
- Enjoy scenic coastal views, from the active Kittery Harbor to the more secluded Seapoint Beach.
- Shop at the Kittery Outlets just off Route 1.
- Learn about history at two historic seaside forts, Fort Foster (now a town park with great trails and ocean views) and Fort McClary, which stood watch from the Revolution through World War I.
Accessible on the Amtrak from Boston + bus, 1 hour 10 min drive
Stop 7: Kennebunkport, ME
There’s no shortage of small town charm on this list (as you can tell), with Kennebunkport being the next stop! This charming small town boasts a picturesque port with plenty to keep you busy, as well as nearby beaches and wildlife preserves that offer something for everyone.
Celebrities are also known to frequent this area. During our visit, Martha Stewart was there just the day before!! We missed her by just one day… Other celebrities known to visit Kennebunkport include Seth Rogen, Sean Penn, Taylor Swift, and the Bush family, who own a compound nearby.
Fun things to do in Kennebunkport:
- Stroll through Dock Square, the historic district, and the harbour, stopping in at shops as you walk, and enjoy the views
- Take a lobster boat or whale watching tour with First Chance Whale Watch
- Drive along Ocean Avenue to see stunning, iconic coastal Maine homes with a stop at the historic St. Ann’s church for coastal views and beauty
1 hour 30 min drive
Image by NT Franklin from Pixabay
Stop 8: Old Orchard Beach, ME
While several places on this list include beaches (this is a coastal drive from Boston to Portland afterall), Old Orchard Beach is a coastal beach town where the main attraction is, well, the beach! Seven Mile Beach means there’s plenty of space for everyone who wants to visit to get a taste of coastal Maine beach life.
The pier here is really unique and something you won’t find at most beaches (in my experience anyway!). It is close to Portland, and you could consider staying in this area instead of in Portland on your trip, where hotel rooms can be very expensive, though the beach can be too in peak season.
While here, check out:
- The only beachfront amusement park in New England, Palace Playland, offering rides and classic seaside entertainment.
- Unique boardwalk and pier with music, lights, and entertainment, creating a lively summer atmosphere.
- Eat your typical New England seaside foods, including the famous Maine lobster rolls, boardwalk fries, and fried dough.
Accessible on the Amtrak from Boston, 1 hour 40 min drive
Stop 9: Cape Elizabeth, ME
Our last and closest stop to Portland is Cape Elizabeth. This town is very charming and a must-stop when headed to Portland from Boston. It’s just 15 minutes away from Portland, meaning you can easily stop here even while spending your time in Portland.
Cape Elizabeth has a quaint, beautiful small town feel, with large historic homes and a charming downtown. There are also six different trails in bays around Cape Elizabeth, so the coastal views are endless here! With the most famous being the trails to Portland Head Lighthouse in Fort Williams State Park.
Don’t miss these spots in Cape Elizabeth:
- Visit the oldest lighthouse in Maine, Portland Head Light, an iconic landmark offering stunning coastal views from the surrounding park, which features walking paths and historic ruins.
- Grab a picnic lunch and stroll the coast in Two Lights State Park with rocky shoreline and twin lighthouses nearby.
Head to Crescent Beach State Park, a mile-long arc of sand and a nice place to relax for a sunny afternoon.
1 hour, 50 min drive
As you can tell, there’s no shortage of great spots to stop on a drive from Boston to Portland, Maine! I hope that this has given you some inspiration for your next trip. I really love New England and all that there is to do in this part of the US. I’m sure you will too!
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