Featuring 1.4 miles of hiking trails, Turtle Head Preserve is a favorite of Holly and Cody's. The main loop circles around the most northern tip of Islesboro. Most of the hike is easy, but some of it is moderate. Along the way are some beaches to explore, views of the ocean, and rocks to climb. You can even see Sears Island to the north across Penobscot Bay. Be on the look out for bald eagles!
The Hutchins Island and Marsh Preserve are a little bit harder to find. There’s only a small pullover with an Islesboro Island Trust sign at the end of Bluff Road to mark the destination. After a short walk down Hutchins Island Ln, you’ll see the trailhead. Then, you’ll come to a junction where you can choose which hike to do. One goes directly to the tidal sandbar and shore. The other is the 1.7-mile Elaine’s Trail around the marsh, which eventually leads to the shore. If you have time, follow the sandbar to Hutchins Island where you can hike the 0.6-mile loop around the island. Just check the tide levels before you cross the sandbar.
On the south end of the island is Islesboro Town Beach near the end of Pendleton Point Road. A sign marks where the rocky beach is, and there’s grills and picnic tables at the edge of the trees. You'll want to catch a picnic dinner and sunset here - it's one of Holly's favorite things to do on the island.
Big Tree Boating is a community sailing program offering classes for all students (ages 10 and older) and abilities, open to all residents and visitors of Islesboro. Holly has fond memories of attending sailing camp here in her youth. Boats are available for recreational sailing from 11 AM to 6 PM during the week and 1 to 6 PM on Saturdays (please call for availability). BTB will close at 4 PM if no one is sailing. BTB is closed on Sundays.
A small, full service grocery featuring fresh fish, meat, and produce, beer and wine, sandwiches and salads, pizza, hard to find cheeses, gourmet products, live lobsters, and Loony's famous baked goods! Be sure to grab a slice of pizza while you're there! Open: 8:30-5:30 M-T & 7:30-7:00 F & S
Convenience store for anything left on the mainland! Open 8:00-6:00pm.
The Dark Harbor Shop is best known for its sandwiches and ice cream. You can even get malts, shakes, sundaes, and soda fountain drinks. On top of that, you can purchase gifts, clothes, and other souvenirs.
Check the Islesboro Community Center website for specific farmers market information!
If you want to learn more about the island in general, head to the Islesboro Historical Society’s museum. It’s located on the second floor of the 1894 Town Hall and features island photos and artifacts of all kinds.
The Summer Shop in Dark Harbor has a beautiful collection of accessories, gifts, and home decor. Also, there are two jewelry designers — Front Shore Jewelry and After Dark.
Find out what events are happening on the island during your stay! You'll find farmers market info, summer concert series, yoga schedules, Pickle ball games, and any other fun goings on! Bonus points for attending a local island event - it's great people watching!
Islesboro Recreation Department was created to provide recreational programming, facilities, and equipment for Islesboro residents and visitors of all ages. Find out what's going on during your stay and get involved with the local community!
Another method of transportation to Islesboro is via water taxi. The Quicksilver company offers water taxi services between Lincolnville and Islesboro a few times a day. You'll find the latest schedule on their website. Captain Ben will be shuttling vendors to mainland throughout the wedding weekend. In addition, you can charter the Quicksilver boat for rides throughout Penobscot Bay. It offers sightseeing tours and other water activities throughout the bay — from Camden to Warren Island State Park.
If you're bringing a boat then check out the town of Islesboro's website for more information on public docking at the ferry landing or Big Tree in Seal Harbor.