One Of Maine's Prettiest Little Port Towns Is An Artsy Haven On A Scenic Trail-Filled Island

No trip to Maine is complete without stepping foot on an island or two. The rocky and dramatic Maine coastline is studded with pine tree-capped islands, islets, and rocks. There are more than 4,600 islands in the state — so where does one even get started? If you're looking for a break from the crowds of Acadia, consider a quieter trip to explore beautiful Deer Isle and the small fishing village of Stonington.

Deer Isle is situated right in the heart of Penobscot Bay, about halfway between Rockland and Acadia. It's a quieter and less visited part of the bay than either of those two destinations and a must-see for art lovers and outdoor enthusiasts thanks to its buzzing art scene and many hiking trails. The major town on the island, Stonington, is the state's largest lobster port. And despite its appeal as an out-of-the-way destination, you can drive there: the island is connected to the mainland via the Deer Isle Bridge, just off State Route 175 and about an hour south of the little city of Bangor.

Stonington is a quintessential Maine fishing village. Tidy wooden homes and businesses line the waterfront, overlooking the lobster boat-packed harbor. In the distance, you can see the rocks and islets of Merchants Row and the larger Isle au Haut farther out. Half of Isle au Haut features one of the least visited, least crowded corners of Acadia park, and the only way to get there is via the ferry that leaves Stonington's wharf.

The center of Stonington looks out over Penobscot Bay from the south side of Deer Isle. Like many working waterfronts in Maine, the community is made of locals who live on the island year-round who welcome a larger group of seasonal visitors during the summer months. The beautiful surroundings inspire artists and travelers from all over the world over, much like other artsy, under-the-radar towns dotted along the Maine coast.

Parallel to the harbor, you'll find a collection of small shops and galleries along Main Street. Browsing each business is always a treat, not just for the treasures you find inside but also for the shops themselves. Walking around Stonington is like walking through a painting, with its neat clapboard buildings and striking Downeast scenery. Watch for the plein air oil paintings in Jill Hoy's gallery, Evelyn Kok's watercolors and pen and inks, and pottery by D. Mortenson. Stonington is also home to Opera House Arts, a community theater that puts on live performances, music, and movies.

Of course, there's a lot more to Stonington than its art scene. Along the waterfront are several popular restaurants where you can get lobster rolls within sight of the boat that caught the tasty crustaceans. There are also inns and bed and breakfasts, should you wish to stay on the island a little longer. The Inn on the Harbor is located right on the water. Other lodging options around the island include Pilgrim's Inn and the Inn at Ferry Landing.

Deer Island is bigger than just Stonington, however. It spans more than 11 miles from the bridge at Little Deer Isle down to town on the far end of South Deer Isle. Along the way there are beaches, hiking trails, nature preserves, and beautiful vistas — enough to make the trip to Stonington an all-day affair.

Start your explorations with a hike around the Barred Island Preserve on the island's western shore. There, a 1.5-mile trail system leads you through a pine forest to a pretty sand beach in a quiet cove. Another preserve to explore is the Edgar M. Tennis Preserve on the east side of the island, which has a 3.4-mile-long trail system. Nearly all trails on Deer Isle are typical of Maine — they're of moderate difficulty with the occasional need to scramble up rocky granite outcroppings. But the topography is great for beginners, and it's a little less strenuous than the hikes farther east in Acadia. For a bigger adventure, you might want to hop on the ferry to Isle au Haut. The island has one of the most remote parts of Acadia, and it's just a few miles south of Stonington.

After you've discovered Deer Isle, you'll want to come back for more. Like the rest of the Pine Tree State, the best time to visit depends on your interests. Prime tourist season is during the warmer months when the hiking and beachgoing are at their best. But winter sports bring people even during the fall and winter, and the island is a sight to behold in the winter. If you are visiting Stonington in the off-season, know that many galleries and businesses stay open through Christmas for holiday shopping.