When you stay at Pilgrim’s Inn, you’ll never run out of things to do! Hike through nature, indulge in farm to table cuisine, and more. Plus, there are many Deer Isle annual events and festivals that happen throughout the year! Whether you happen to catch one during your stay at Pilgrim’s Inn or are planning your vacation around one of them, we’ve chosen our favorites.

If you’re planning a trip to Downeast Maine, take advantage of our complimentary Vacation Guide. Planning a vacation can be challenging, so we’ve chosen our favorite things to do in the area to save you from hours of research! Skip the tedious part of preparation and use our free guide to find:

  • The best restaurants in the area
  • Outdoor activities for all skill levels
  • Cultural events, museums, and entertainment
  • Festivals, attractions, and Deer Isle annual events you won’t want to miss

Deer Isle Annual Events

Wings, Waves & Woods

Wings, Waves & Woods Weekend is an annual birding festival that draws people from all over New England to watch birds returning north from their warm winter retreats. Register for the festival to get a bird list, information on local nature preserves, an Island Guide, and coupons for local businesses. It’s the perfect way to celebrate the return of spring weather!

4th of July

Start celebrating the 4th of July in Deer Isle by watching the annual parade that goes right by Pilgrim’s Inn! After a day filled with fun, make your way to Stonington Harbor to watch the fireworks display light up the night sky.

Fisherman’s Day

Every July, locals and visitors look forward to Fisherman’s Day. During this fun event, you’ll experience a day full of traditional activities like trap hauling demonstrations, a codfish relay, a rowboat race, pet show, watermelon eating contest, and more. Indulge in delicious, fresh seafood throughout the day between watching events!

Stonington Lobster Boat Races

Stonington Lobster Boat Races

The Stonington Lobster Boat Races are an annual summer spectacle in Maine. Throughout the season, boats speed through different locations. Check the schedule for when they will pass through Stonington, then book your stay at Pilgrim’s Inn! The races start with a pancake breakfast in the morning and delicious crab meat rolls after the event to celebrate.

Haystack Open Studio and End of Session Auctions

The Haystack Mountain School of Crafts, a renowned arts school, offers summer programs each year. At the end of each session, students are invited to donate artwork to the Haystack Open Studio and End of Session Auctions. Visitors are allowed to partake in these auctions; proceeds go toward the scholarships and school improvements.

Shakespeare in Stonington

Every year, supporters of the arts wait patiently for Shakespeare in Stonington. The Stonington Opera House puts on 3 productions during their summer theater season, the last being an epic evening of Shakespeare. The play chosen rotates each year!

Blue Hill Fair

During your stay at Pilgrim’s Inn, go to a true county fair. Every year, the neighboring town of Blue Hill puts on the Blue Hill Fair. Here, you can indulge in fun, games, carnival rides, and delicious fair food.

Castine Plein Air Festival

Every July, local artists gather in Castine for the Castine Plein Air Festival. For 3 days, artists paint from early morning until sunset throughout the lovely village of Castine. Art lovers are invited to stroll around the town, observing artists as they work to capture the scenes in front of them. Then, a reception and art sale takes place on the last day of the festival.

Eggemoggin Reach Regatta

The Eggemoggin Reach Regatta is an annual summer tradition in Maine. Every August, over 100 wooden boats sail up the coast of the small town of Brooklin. What blossomed from tradition is now an extravaganza that visitors come from all over the world to participate in.

Deer Isle Lighthouse TrailMaine Open Lighthouse Day

Many wonder about the lighthouses scattered across Maine. These historic structures have kept mariners safe for generations, but now their towers are usually closed to guests. However, for one special day out of the year, they are open. Locals and visitors from all over the world wait patiently for Maine Open Lighthouse Day when they can finally go inside and explore!

Deer Isle Stonington Fridays

During Deer Isle Stonington Fridays, also known as DIS Friday, the community comes together to offer locals and visitors something special. Participating shops in Deer Isle Village offer special discounts, delicious food is offered, and pop-up markets are held!

Pilgrim’s Inn is Your Vacation Destination

Now that you have discovered which Deer Isle annual events you want to attend, explore the cozy accommodations at Pilgrim’s Inn to start planning your stay!