4 of the Best Stops on a Boston to Boothbay Harbor Road Trip

For many people, city life has its charms. In urban areas, there’s plenty of excitement and countless things to do. However, everyone needs a change of scenery every once in a while! In New England, the best way to escape the hustle and bustle of the city is to go on a road trip. For those who live in Boston, there’s no better place to hide away than Boothbay Harbor, Maine. This coastal destination is just three hours north but feels worlds away! Here are four stops to make along the route from Boston to Boothbay Harbor.

After a Boston to Boothbay Harbor road trip, you’ll want to experience life in Midcoast Maine through the eyes of a local! The perfect way to do so is to consult our complimentary Vacation Guide. We created this easy-to-use resource so visitors can spend less time planning and more time exploring. Request access for free today and learn all about the best things to see and do in the region!

Boston to Boothbay Harbor: A Road-Tripper’s Guide

About the Route

Every now and then, Bostonians dream of escaping the daily grind and finding a place where they can simply relax. A short road trip from Boston to Boothbay Harbor offers sweeping coastal views, historical points of interest, and plenty of photo opportunities. Whether visitors want to drive straight to Maine’s stunning Midcoast region or make a few stops along the way, this scenic, three-hour drive offers the perfect amount of serenity. Here are our four favorite stops to make during this road trip.

4 of the Best Stops to Make on a Boston to Boothbay Harbor Trip


After leaving the crowds and city noises of Boston behind, it’s time to hit the road! About one hour into the drive, be sure to make a quick stop in Salem, Massachusetts. Known as the infamous site of the 1692 Salem Witch Trials, this haunting spot is perfect for history buffs. In addition to monuments like the Witch House, we recommend checking out the Stickworks Statues or the Salem Common park.


About an hour and 45 minutes after departing from Salem, you’ll come upon Portland, Maine’s largest city. This is an optional stop (since it, like Boston, is an urban hotspot), but a noteworthy place nonetheless. Portland offers microbreweries, window shopping on Commercial Street, and plenty of art museums.

Boothbay Harbor

The final leg of this quick and enjoyable road trip is Portland to Boothbay Harbor, Maine. There is no shortage of things to do in and around Boothbay Harbor. Love golf? There are several courses nearby. Need a little retail therapy? Stroll in and out of local shops and find handcrafted products. Hungry? There are fantastic restaurants and lobster shacks just around the corner. Boothbay Harbor is also a boater’s paradise, so be sure to rent a boat or go kayaking during a stay here. Beach lovers will also delight in the area’s array of historic lighthouses (like the Pemaquid Point Light) and rocky coastlines.

Newagen Seaside Inn in Southport is Just Around the CornerBoston to Boothbay Harbor

The best place to rest and relax in Midcoast Maine is Newagen Seaside Inn! One of the Boothbay Harbor region’s best-kept secrets, this locally owned inn on Southport Island offers a luxurious waterfront experience found nowhere else in the area. Choose between a private cottage or a traditional guest room, both of which feature views of the ocean, premium amenities, and access to the inn’s on-property restaurant, The Pub. The resort is open between May and October, so don’t miss the chance to experience beautiful Southport this year!

Instead of ending a Boston to Boothbay Harbor road trip at a hotel, check our availability today and start looking forward to a truly unique experience in Midcoast Maine!