Find all the best things to do in Deer Isle, Maine during your stay!

Scenic routeRocky coastline, quiet coves, and breathtaking landscapes greet visitors at every turn on Deer Isle in Penobscot Bay. As a guest at Pilgrim’s Inn, you can explore nearby nature trails, take kayaking excursions to surrounding islands, travel to Isle au Haut and Acadia National Park, visit inspiring art galleries, or take classes at the world renowned Haystack Mountain School of Crafts.

We are also a perfect base for taking Maine scenic drives along the coast and exploring the beautiful towns of the Blue Hill Peninsula. Along with all the best Deer Isle attractions, there are also plenty of things to do in neighboring Stonington, Maine.

Pilgrim’s Inn is one of the best places to stay in Downeast Maine because there really is something for everyone to enjoy! Read this list of our favorite things to do in Downeast Maine, including Deer Isle attractions and Stonington activities.

Also, be sure to download our Free Vacation Guide for even more things to do in Deer Isle, Maine during your visit with us!


For those who love the outdoors, Deer Isle is the perfect place to visit. Hiking trails and nature preserves offer visitors a glimpse of stunning landscapes and local wildlife as they experience the island. Visit the Island Heritage Trust for more information.

Kayaking, Fishing & Charter Boat Tours

Sailing in MaineKayaking along the coast of Deer Isle is one of the best experiences to enjoy during your vacation! 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, while Driftwood Kayak features personalized full-day kayaking sessions, including overnight camping trips to the beautiful surrounding 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, attracting 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 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. Acadia offers a number of things to do in Downeast Maine, from rigorous hikes to scenic drives or educational tours. For official information about the park, please visit the National Park Service Website.

Isle au Haut, part of Acadia National Park, can be reached by boat from Stonington. The island is an enchanting place to explore on mountain bikes or by foot and makes for a splendid day trip. Read about the Isle au Haut ferry for more information on planning your trip.

Things To Do in Stonington, ME

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 things to do in Stonington, ME.

Artists, Art Galleries & Haystack

Turtle GalleryOur scenic island has been attracting visual artists for decades, resulting in dozens of art galleries to tour such as the local Turtle Gallery. 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, read about the Deer Isle Artists Association.

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

The vibrant community of Deer Isle offers a range of cultural activities to visitors and residents alike. The Stonington Opera House hosts many programs, including a summer jazz festival, annual radio variety show, “Shakespeare in Stonington,” 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.

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 at this Island Country Club, have lunch at the Fairway Cafe and enjoy the relaxed atmosphere of this island gem.

Blue Hill Peninsula

During your stay at our Downeast Maine bed and breakfast, venture over to the Blue Hill Peninsula and visit the towns of Blue Hill and Castine. For an added expedition, take a scenic drive through Brooklin, Brooksville, Sedgwick, and Penobscot, stopping along the way at antique shops and old-time general stores. Blue Hill is also host to the famous Blue Hill Fair, the inspiration for the fair in Charlotte’s Web!

There is never a shortage of things to do on Deer Isle, Maine! And, when you stay at Pilgrim’s Inn, you will be nearby all of these local activities and attractions. For even more information on things to do in Deer Isle, Maine, download our free Vacation Guide, then find your room!