Much of life is about the journey, not necessarily the destination. There is a great sense of relief when the goal is reached and the finish line is crossed, but sometimes, however, the beauty of the journey itself can be lost in this pursuit. We here at The Craignair Inn by the Sea have resolved to help make it as enjoyable as possible with travel tips and fun stops along the route for the ultimate weekend getaway from Boston to Midcoast Maine.


Explore Freeport

A beautiful coastal town situated about two hours away from Boston, Freeport is the perfect place for your first detour! All parking in the city is free all-day, so you can stay and shop to your heart’s content without having to worry about additional expenses. Check out local shops as well as outlet stores and choose from a wide variety of places to visit. Stop by the beach and admire the view, go for a walk and stretch your legs, or even visit the Maine Maritime Museum and learn all about the area’s deep nautical history. We also recommend Bow Street Market to recharge your batteries with a delicious meal from one of Freeport’s many excellent eateries. They are a unique destination that houses a butcher shop, specialty grocer, liquor store with a wine cellar, and a full to-go menu of savory hot and cold freshly made sandwiches, pizza, and more.


Tour Boothbay

Another hour up the road is Boothbay, a charming little town with a long history of fishing from the rich waters of Linekin Bay. Take a walk through downtown and breathe in the crisp ocean air, check out local artisans, and break up your trip with a refreshing change of pace. Stop and smell the roses at the Coastal Maine Botanical Gardens and explore a lush space with over 300 acres of plant life and native butterflies. They also house a bee exhibit where you can see the garden’s bee population in action while learning all about their essential role in the garden’s ecosystem.


Spot Beautiful Lighthouses

Just a 20-minute drive away from Boothbay and a small detour off the main road is Pemaquid Point Lighthouse, one of our favorite lighthouses in the area. See stunning views from the cliffs and even go inside the lighthouse if the weather permits. It’s a great stop for a photo op with the potential for some incredible pictures, especially during golden hour and at sunset. Visit the learning center and discover the history of this important landmark as well as an art gallery featuring inspired renditions of the lighthouse itself. There are lots of other lighthouses to see once you’ve reached the Craignair and Pemaquid Peninsula is the perfect place to start your lighthouse adventure right!


Unwind Away From the City

Make your weekend getaway from Boston unforgettable with the best end to a journey you could ask for, a sublime stay at our Midcoast Maine bed and breakfast. Instead of exhaustion from a long continuous car drive, now you have a lovely experience to look back on from exploring the coast on the way up. Cozy accommodations await with all the amenities you need for a fantastic staycation here in Spruce Head. Comfortable king and queen beds, private balconies with ocean views, and a historic ambiance inspired by New England maritime traditions. Celebrate your arrival with a mini-bottle of Perlage Prosecco perfectly split for two and cheers to the satisfying conclusion of a memorable trip that is only just getting started!