Friday
Afternoon
Sunset on the beach

The sun is about to set as I cross over the Deer Isle Bridge to Little Deer Isle, then follow the causeway to Deer Isle. Once on the island, I head to Sand Beach, a small public cove located five minutes from Stonington village. I walk along smooth granite rocks and listen to Mark Island Light sound in the distance.

Evening
Dinner by the sea

The mosquitos start buzzing, forcing me to leave the sandy cove and drive back to the town of Deer Isle. Nestled between Northwest Harbor and Mill Pond sits the Pilgrim’s Inn, my home for the weekend. The inn, listed on the National Register of Historic Places, was built in 1793 as a private residence and became an inn in 1890. Over the past three decades, the building has gone through several renovation projects. However, the charm and character remain in the tin ceilings, wide pumpkin pine floors, and eight-foot-wide fireplaces. There are 12 guest rooms and three cottages that look out to the inn’s backyard, which runs along Mill Pond.

After checking into my room, I drive to Aragosta at Goose Cove to meet my mother, Lisa, for dinner. A vine of yellow and purple flowers frames the entranceway. Inside is a large fireplace and long horizontal windows that provide panoramic views of Goose Cove. Once seated, we order two glasses of red wine and an appetizer of Blue Hill Bay mussels. As we wait, executive chef and owner Devin Finigan sends us a tasting plate of lobster ceviche served in tiny shells, corn salsa topped with pickled shallots, fresh snap peas, and Spanish tortillas. We also order a fresh beet salad and a cheese board, which features cheeses from Yellow Birch Farm, duck liver pâté, cornbread served in a small skillet, and grilled pear. For our main course, we choose the Bagaduce Farm duck and Deer Isle halibut. We savor both meals until it is time for dessert, which consists of chocolate mousse covered in a hard chocolate dome that is topped with edible gold flakes.

Saturday
Morning
Early-morning walks and local hangouts

Before breakfast, my mother and I walk around Lily Pond Park in Deer Isle. We search for wild mushrooms and flowers along a path that runs adjacent to the water. Hungry from the early-morning excursion, we drive into Stonington village and have breakfast at Harbor Cafe, the local diner. We order a vegetable omelet and oatmeal topped with fresh berries.

In need of a pick-me-up, we walk a few doors down to 44 North Coffee, which is bustling with locals and tourists taking advantage of the cafe’s Wi-Fi. My mother orders a cup of coffee from the company’s roastery in Deer Isle, and I choose a cup of loose-leaf green tea from Tempest in a Teapot.

Across the street is Stonecutters Kitchen and Harbor View Store. Inside, we fill our cooler with two grilled chicken sandwiches and meet a group of local fishermen who order lobster rolls and coffee to go.

Afternoon
Kayaking, an island picnic, and hiking views

The ocean is calm, so we rent two kayaks from Old Quarry Ocean Adventures in Stonington. Because the water temperature is in the low 50s, we put on wetsuits before pushing off from the landing. As we paddle through Webb Cove, we navigate around small rocky islands and spot a seal bobbing its head above the water.

We find a beach on a nearby island. After pulling our kayaks onto the shore, we lay our towels on the sand and enjoy sandwiches and iced tea in our quiet hideaway.

After kayaking, we stop at the Barred Island Preserve trailhead in Deer Isle. This mile-and-a-half hike leads to a sandbar that is exposed during low tide, allowing hikers to walk across to Barred Island. When we arrive, the tide has already covered the sandbar, so we hike to an overlook and see sweeping views of Goose Cove.

Evening
Historic opera house and pizza on the pier

We head back to the inn and relax on the back deck before driving into Stonington. At the Stonington Opera House we meet Opera House Arts’s new producing executive director, Per Janson. The opera house is listed on the National Register of Historic Places and dates back to the early twentieth century, when it was a vaudeville house for traveling performers. The nonprofit restored the building two decades ago and reopened it as a year-round theater that offers live theater, music, dance, film, and events for the island community.

In the heart of Stonington is the new Acadia House Provisions. This seasonal restaurant is an outpost of chef Ryan McCaskey’s two-Michelin-starred Acadia Restaurant in Chicago and serves lunch and dinner. McCaskey has been visiting Deer Isle in the summer since he was a child. The restaurant isn’t opening until two days after we leave the island, so we go back to Stonecutters Kitchen to order an 18-inch Green Island pizza and share it on a picnic table that overlooks Stonington’s commercial fish pier.

Sunday
Morning
Breakfast at the inn and art in the village

We wake to the sounds of birds chirping and make our way downstairs to the inn’s dining room. Breakfast consists of scrambled eggs topped with fresh herbs from the kitchen garden, sausage patties, and toast with jam. After we eat, we finish our tea and coffee while walking around the inn’s gardens.

The forecast calls for rain, so we drive into Stonington to peruse the art galleries and shops. Tucked away from the village in a rustic white barn is the Jill Hoy Gallery, filled with whimsical paintings of the coast of Maine. We also stop into J. McVeigh Jewelry, a gallery owned by John McVeigh, a professional opera singer who creates jewelry out of recycled metals, gemstones, and fossils.

Afternoon
Rainy-day tea with jam

It starts to rain, so we drive to Nervous Nellie’s Jams and Jellies in Deer Isle. The shop is surrounded by a garden of life-size metal dragons, knights, people, and birds created by local sculptor Peter Beerits. We taste five flavors of jam and chutney on warm scones and drink cups of organic hot tea. Before leaving, we purchase jars of our favorite spreads and three handpainted dishtowels.

On our way home, we stop at Causeway Beach, a public beach located next to the bridge that connects North Deer Isle to Little Deer Isle. There, we meet a couple playing fetch with their dog and look out across Penobscot Bay one last time before crossing the bridge and leaving the island.