Travel Guide: Squirrel Island, Maine

Hello all!

I’ve been a bit off the grid this month – after quitting my job, I immediately headed north to Connecticut for my childhood best friend’s wedding, spent a week with family in Maine, and then returned to CT to sort through/pack up my childhood home before I start grad school at the end of August. To say the past few weeks have been a whirlwind would be an understatement!

I’m excited to get back into a flow of blogging and posting, so to start I’ll be playing catch up on my August adventures in Maine on Squirrel Island. This was my first time back in Maine after doing college tours over a decade ago (long time no see, Bates and Bowdoin) so I was very excited to return and actually spend time in this beautiful state. I loved that we were staying on the secluded Squirrel Island (disclaimer: there are no actual squirrels on the island – it is however shaped like a squirrel) but had access to the cute little coastal town of Boothbay Harbor if we wanted to eat out, shop, or peruse galleries filled with local artists. I’ll be sharing a bit of my experiences both on the island and in the quaint little town to show all this area has to offer.

As this harbor town and island are located off the coast of Maine, it’s easiest to take a scenic drive along the New England coastline and park in the town before ferrying over. It was a lovely trip to get to the island – simply jam out to your favorite tunes or pop in an audiobook as you cruise on Maine’s 70 mph highways!

I love New England year round, but I’ve especially come to appreciate the summer months up north after living in the sweltering, humid, hellish DC summers the past five years. The 80 degree days are perfect for lounging outside, but I love when the temperature drops to be cooler at night so you can get cozy before falling asleep. If you’re looking for a great time to take a trip up north to Maine, August is a perfect month to do so!

While I was mainly spending time with family and relaxing on the more remote Squirrel Island, we did get a few opportunities to explore the mainland. Hopefully I’ll be back again soon to give a more fleshed-out guide to this part of the state, but in the meantime please enjoy this mini guide based on my week in the area!

What to do:

  • Ferry Ride – the ride to and from Squirrel Island actually includes a boat tour where you can learn more about the local area and surrounding islands. There are a lot of small docs hosting boat tours to a lot of the other islands near the coast as well, so you can truly explore a lot!
  • On Squirrel Island, there are lots of beautiful beaches to enjoy and walking paths to traverse, as well as a beautiful library where you can add to the community puzzle or play a game of tennis on the local courts. I’d highly recommend taking a stroll through the fairy forest that features miniature fairy homes decorated by the islanders – it’s so quaint!
  • In Boothbay Harbor, there are tons of art galleries and cute shops to explore. I’ll share a few of my favorites below in the “where to shop” section. There are also breweries, a local library, and plaques located around the town so you can have a casual walking tour while learning about the town’s history!

Where to eat:

  • Squirrel Island only has one restaurant – The Tea Shop – that features delicious local fare including delicious salads, sandwiches, and soups of the day, as well as an adorable little ice cream shop. They also have a community garden you can donate to and then pick from to add to your at-home meals!
  • In Boothbay Harbor, you can find a range of delicious cuisine:
  • Kaler’s Restaurant (for authentic lobster rolls and New England fare in a fun, casual setting)
  • Bet’s Famous Fish Fry (only open for a few hours at lunch, this delightful local staple has a select menu of about 4 items featuring fresh catches each day – when they run out, they close down!)
  • Ports of Italy (absolutely delicious Italian cuisine!)
  • Footbridge Brewery (a charming, hole in the wall brewery that features a great selection of delicious beers – I recommend the potent Trapdoor to start!)
  • Brisetto’s Second Cup (for sipping coffee with the best view to people watch the docks)

Where to shop in Boothbay:

  • For Souvenirs: The Hutch or Shirts by the Bay
  • Sherman’s Maine Coast Bookshop
  • Coastal Maine Popcorn Co.
  • Gimbel & Sons Country Store
  • Finest Kind
  • Eventide Epicurean Specialties
  • Enchantments
  • The Ritz Estate Jewelry

I hope this mini guide inspires you to visit Boothbay Harbor or Squirrel Island during your next vacation or trip to Maine! Let me know if you’ve ever been here in the comments, too!



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