Things To Do

PLACES TO EAT

Big Island Grill

This food truck is a delicious lunch and dinner option. Find it in the park across the Main Rd. from the community center.

The Dark Harbor Shop

Catch the last weekend of the summer for this seasonal island favorite. This historic ice cream shop was one of Rosie's teenage summer jobs and remains a hot spot of the island social scene. Also available for lunch and breakfast (limited menu)

Island Market

Buy groceries or prepared food from this beloved island landmark!

Islesboro Community Center Cafe/Gym

Come workout at the gym for very affordable guest rates or get a bite at the cafe.

Durkee General Store

Up Island grocery store and sandwich shop.

SWIMMING AND HIKES

Turtle Head

A gorgeous short hike at the northern most point of the island with breathtaking panoramic views. Budget 45 minutes to an hour.

Hutchins Island

Explore a small island with incredible geology that is connected to Islesboro via tidal sandbar only at low tide. Budget about 2 hours

Pendleton Point

Check out more incredible rock formations and gorgeous panoramic views at the islands southern most point. Seriously the island is full of amazing geology! Short hike

Big Tree Beach

This is the town beach, and a nice one for swimming.

SHOPPING

Apple's

At the corner of Pendleton Point Road and Babbidge Road., Islesboro, ME, United States, Maine. A tiny shop devoted to the style of famed interior decorator, Sister Parrish.

The Summer Shop

A shop for all your preppy interior decor and gifting needs!

Main(e) Point Books

This book shop is nestled between the Dark Harbor Shop and Summer Shop

ACTIVITIES

Islesboro Historical Society

A fascinating museum devoted to the history of Islesboro is on the second floor. Rotating exhibitions on the ground floor.

Pripet Riding Program

House stable offering riding lessons and trail rides in a beautiful meadow overlooking the ocean. Book in advance.

Alice L. Pendleton Library

An adorable and historic town library, offering a pleasant place to work remotely.

Tarratine Golf Club

If you are interested in scheduling a round of golf, let us know and we will do our best to facilitate.

Double Door Gallery

An art gallery featuring primarily Maine artists in rotating exhibitions.