maine coastal road trip

A Guide to Your Next Maine Coastal Road Trip

Maine is notorious for its rocky coast, salty air and fresh seafood, wonderful any time of year but especially beautiful in summertime. Now is the time to plan that trip to take advantage of your active retirement and explore the oceans, mountains and forests that can be found along the coast! Not only is a Maine coastal road trip perfect for a socially-distanced getaway, it allows you to plan for something fun to look forward to in warmer weather!

Below, we’ve put together a general guide to the must-see stops along your road trip route!


There is no better starting point for your Maine coastal road trip than the bustling city of Portland, where you can literally smell the salty ocean air as you peruse the cobblestone streets. Spend a day walking around the quaint streets, stopping in the boutique shops, art museums such as the renowned Portland Art Museum, and one of the many famous restaurants. There’s something for everyone in this charming seaside city!


Next stop? The lovely Freeport, Maine! You may know of Freeport for it’s L.L. Bean flagship store with the enormous, iconic Bean boot out front, but there’s much more shopping to be had! There are nearly endless outlet stores, all within walking distance from each other, where you can shop your heart out…at a discount! There are plenty of restaurants to choose from if you get hungry, including the newly-renovated Maine Beer Company, which boasts incredible pizza, even better brews and 1% for the planet.


Cumberland, Maine is a beautiful community with a wide variety of activities to take advantage of. With a rich history, you can check out staples such as the Cumberland Historical Society or Prince Memorial Library to get your dose of local education. Take a long walk at the Twin Brook Recreation area or play a round at the gorgeous Val Halla Golf Course. If you’re looking for a beach day, head to Broad Cove Reserve to enjoy the views of the Casco Bay. There is no better town for a day of activities! While you’re in town, call for a fun tour of Cumberland Crossing by OceanView, our active retirement community with spacious cottages!


Camden is one of the best small towns in Maine for active seniors, with its idyllic harbor, seemingly endless seaside hiking trails, delicious fresh seafood and local boutique shops. Hike up to the top of Mount Battie – an easy hike about a mile each way with stunning views of the harbor. Once you get to the bottom, treat yourself to a jumbo lobster roll, briny oysters and a cold beer (brewed right in town!), then spend the rest of your day taking a leisurely stroll through the beautiful street and getting a little shopping in.

Bar Harbor

If you can get there in time, drive straight to the top of Cadillac Mountain in Acadia National Park – it’s the first place the sun rises in the country and is truly a bucket list item to witness. 

From there, rent bikes (or bring your own!) and ride the beautiful old carriage trails with breathtaking views of Eagle Lake or head to the Jordan Pond House for their famous popovers. Looking to get a hike in? The Beehive Loop Trail is a moderate yet breathtaking option, with gorgeous views of the ocean and some more challenging sections that include climbing iron rungs. If driving the scenic Park Loop Road, be sure to stop by Thunder Hole, the local seaside cavern that booms when the waves of the Atlantic come crashing in. 

After you’ve explored Acadia to your heart’s content, head back to downtown Bar Harbor for a little shopping and dinner. There are many wonderful restaurant options, but you can’t go wrong with Geddy’s – this kitschy local spot has been serving mouthwatering pub food, fresh seafood and cold beers for over 40 years! 

Cumberland Crossing by OceanView

Maine’s stunning coast has so much to offer, we guarantee there’s not a single stop you’ll be disappointed with along your Maine coastal road trip! 

At Cumberland Crossing by OceanView, we’re located right near the coast in beautiful Cumberland, Maine. Our active retirement community provides endless opportunities for you to enjoy the freedom of your retirement years, without the stress or hassle of maintaining a home. Learn more about our cottages and maintenance-free living by contacting us at Cumberland Crossing today!