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Things To Do

Deer Isle in Penobscot Bay offers you the very best of coastal Maine. Rocky coastline, quiet coves, and beautiful views greet visitors at every turn. As a guest at Pilgrim's Inn you can explore nearby nature trails, take kayaking excursions to surrounding islands with licensed guides, travel to Isle au Haut and Acadia National Park, visit our numerous art galleries, or take classes at the world renowned Haystack Mountain School of Crafts. We are also a perfect base for taking scenic drives along the coast and exploring the beautiful towns of the Blue Hill Peninsula.


For many people who love the outdoors, Deer Isle is the perfect place to visit. Hiking trails and nature preserves offer visitors a great way to experience the island. Visit the Island Heritage Trust for more information.

Kayaking, Fishing and Chartered Boat Tours

Kayaking along the coast of Deer Isle is an experience not to be missed! Over 60 islands offer unlimited opportunity to explore, making Deer Isle one of the hottest kayaking destinations along the Atlantic coast. Old Quarry Ocean Adventures offers guided kayaking trips for any level, or will rent you kayaks to explore the islands on your own. We also recommend Driftwood Kayak for personalized full day kayaking trips, including overnight camping trips to our beautiful islands. For eco-tours aboard a lobster boat we recommend a private, customized tour with Guided Island Tours with licensed Maine guide Captain Walt Reed. Old Quarry Ocean Adventures also offers afternoon eco-tours and sailboat rentals. For shorter trips Isle au Haut Boat Services has boat trips in the afternoon that do not require advanced reservations. Sailing the waters of Penobscot Bay is an unforgettable experience. Long considered some of the best sailing in the world, Penobscot Bay has attracted sailors to this region for centuries. We recommend Guildive Cruises for a day sail out of Castine, and can provide you with information on additional cruises in our area upon arrival. For half day (great for kids) and full day ocean fishing adventures with a licensed Maine guide, contact Eggemoggin Guide Service. For inland fishing trips contact, Dave’s Guide Service.

Acadia National Park & Isle au Haut

A visit to Downeast Maine would not be complete without a trip to Acadia National Park. Located just over an hour from Pilgrim's Inn, the park encompasses 47,000 acres of coastal shoreline, granite-topped mountains, wooded areas, bogs and spectacular scenery. The park offers something for everyone from rigorous hikes to scenic drives or educational tours. For official information about the park, please visit the National Park Service Website.

Isle au Haute, part of Acadia National Park, is reached by boat from Stonington on Deer Isle, just 6 miles from Pilgrim's Inn. The island is a great place to explore on mountain bikes or by foot and makes for a memorable day trip. The island can be reached daily by boat from Stonington, go to Isle au Haut Boat Services for more information.


Named for the granite industry that made it famous, Stonington is also home to the most productive lobster fishing port along the Maine coast. No trip to Deer Isle would be complete without visiting this picturesque port and tasting a Deer Isle lobster! Visit the Deer Isle-Stonington Chamber of Commerce Website for more information about local events and activities in Stonington.

Artists, Art Galleries and Haystack

Our picturesque island has been a draw for visual artists for decades, resulting in dozens of artist galleries for you to visit. In addition, the world renowned Haystack Mountain School of Crafts is located just a few miles from the Inn. To learn more about the artists and galleries on Deer Isle, go to Deer Isle Artists Association Website. To learn more about Haystack Mountain School of Crafts go to Haystack Mountain School of Crafts Website.

For a guide to the arts, dining and other attractions on the Blue Hill Peninsula and the islands, please visit the Arts Guide Website

Music, Film, Theater & Dance

Deer Isle is a vibrant community offering a range of cultural activities to visitors and residents alike. The Stonington Opera House now offers the community a diversity of programs from a summer jazz festival and annual radio variety show, to “Shakespeare in Stonington” to dance workshops and films. Visit Opera House Arts for current listings.

Just 25 minutes from Deer Isle is the famous Kneisel Hall, known for being the “cradle of chamber music teaching in America”. Kneisel Hall in Blue Hill features outstanding chamber music concerts all summer long. Go to the Kneisel Hall Chamber Music School and Festival Website for more information.

Tennis & Golf

Deer Isle has a country club with a 9 hole golf course and three tennis courts which are open to the public. After a round of golf or a game of tennis, have lunch at the Fairway Cafe and enjoy the relaxed atmosphere of this island gem. Find out more on the Island Country Club Website.

Blue Hill Peninsula

Exploring the Blue Hill peninsula and visiting the towns of Blue Hill and Castine, or taking a scenic drive through Brooklin, Brooksville, Sedgwick and Penobscot, stopping along the way at shops and old time general stores is a wonderful way to fill your day. Visit the Blue Hill Peninsula Chamber of Commerce Website for more information.


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Cadillac Mountain by Terrell S. Lester
Sheep Island Sunset by Terrell S. Lester
Father and Son by Terrell S. Lester