Four Ways to Enjoy Your Boston to Maine Road Trip

Mix things up every once in a while and venture out from your hometown to explore a nearby destination! We invite you to take a few days to experience the ultimate Boston to Maine road trip. Grab your better half and drive up the East coast. Once you arrive, an endless list of adventures awaits! Stop to snap pictures at scenic lighthouses, indulge in local cuisines, and enjoy stunning waterfront views. Pack your bags, fuel up your car, and get ready for the trip of a lifetime.  

If you need help filling up your itinerary, we have plenty of more recommendations in our free Vacation Guide. We included the absolute best things to do and places to see when you arrive in Maine. Get your guide now — you can even reference it while passing the time in the car.  

Plan the Ultimate Road Trip  

Why Boothbay Harbor Is the Perfect Destination for Your Boston to Maine Road Trip  

Aerial view of the area showing the things to do in Boothbay Harbor

If you’re coming from the Boston area, consider choosing Midcoast Maine as the final stop on your road trip. Boothbay Harbor is a scenic, waterfront village offering a relaxing escape from the hustle and bustle of the city. To start your Boston to Maine road trip, head north along I-95, I-295, and Route 1 for a remarkable coastal adventure. From start to finish, you can expect about three hours of driving time over 168 miles.  

The Best Things to do in Boothbay Harbor, Maine

The true Maine experience begins when you arrive in Boothbay Harbor. Our coastal village is home to a wide variety of attractions and things to do. Whether you’re searching for excitement or relaxation, there’s something for you here. To get a taste of our local culture, plan your trip around some of our festivals, like Windjammer Days and Boothbay Harbor Fest. If you’re not sure where to start and want to leave the planning to us, take a look at our five-day Maine itinerary! 

Tour a Nearby Lighthouse  

Burnt Island LighthouseMaine has been nicknamed the lighthouse state for many reasons, one of them being that there are more than 60 beacons of light dotted throughout the entire region. With so many lighthouses in the area, you will encounter one sooner rather than later. One of our favorites is the Burnt Island Lighthouse. This beacon is the second oldest surviving lighthouse in Maine, and you can see it right from the inn. 

Go Whale Watching  

Whales in Boothbay Harbor

There are a number of whale types you might spot during a whale watching adventure in Midcoast Maine, including humpback whales, pilot whales, minke whales, and fin whales. The season usually begins in mid-April when these fantastic creatures migrate north for their feeding season. The best way to enjoy a whale-watching excursion is with an experienced tour company that can take you to the region’s best whale watching locations. The best part? In addition to whales, you may even spot dolphins, seals, and other wildlife!  

Enjoy Fresh Maine Lobster  

Lobster Tails with lemon wedgeIn Boothbay Harbor, you’ll find some of the freshest lobster in the United States, but where will you find the best dishes? Kaler’s Lobster House has precisely what you are looking for. From lobster rolls to lobster B.L.Ts, this restaurant prepares some of the best seafood in Boothbay Harbor. Alongside your tasty meal, you will also get to enjoy harborside dining in a relaxing atmosphere. 


The Best Place to Stay When You Arrive

The bed inside Room 15 in the Windward Guest House at Topside Inn

Topside Inn is a remarkable place to stay in Boothbay Harbor, but you don’t have to take our word for it. Read through some of our reviews and media mentions to see the type of experience and level of service you can expect. Our Inn features stunning views of the harbor, top-notch accommodations, and a long list of amenities like gourmet breakfasts with ingredients from our on-site gardens

Consider Room 15 for your relaxing getaway at Topside Inn. This recently remodeled space features a bright, modern feel in a coastal environment. Relax on your luxurious, king-size bed and enjoy unmatched views of the harbor and sunsets from your covered sitting porch. It’s the ideal place to end up on your Boston to Maine road trip.

Check our availability and book your stay today!