5 fun things to do in Eastport

Eastport’s Hidden Gems, According to a Local Artist

Eastport, Maine – the nation’s smallest city, with just 1,300 residents as of the 2020 census, is still a vibrant place for those who know where to look. One of those who have found the city’s charm is Amy Ray, a native of Eastport who returned to her hometown after more than three decades living in New York City and California. Ray, who was born in the city in 1961, and her husband, bike‑repair entrepreneur Mike Stewart, have called Eastport home for the past six years.

Ray runs Bingville Style Stop, a boutique that opens each spring and stays open through the holiday season. The shop offers vintage clothing, upcycled pieces and a line of wearable art designed by Ray herself. Stewart’s bike rental and repair business is located just a short walk away in downtown Eastport, giving the couple a quiet, community‑focused lifestyle.

When asked about the places she loves in her city, Ray’s enthusiasm was palpable. “My favorite place to grab lunch and a coffee is definitely Picnic Café & Bakery on Water Street,” she said. “They have fresh sandwiches, yummy pastries and great coffee served by the nicest owners and crew around. I particularly love their breakfast wraps.” The café, located on Water Street, has been a staple of Eastport’s downtown food scene for years.

For a cool drink on a hot day, Ray turns to The Polar Treat, a local ice‑cream parlor that has been a tradition for 70 years. “It’s definitely the place to be on a hot day for an ice‑cold root beer float or coffee milkshake. It is owned by a lovely family, and their service is consistently cheerful and efficient,” she added. The shop sits just off the island on Route 1 in Perry.

Shopping locally is a priority for Ray, and her favorite boutique is Friend of a Friend, located at 89 Water Street. “My favorite shop hands down is Friend of a Friend at 89 Water Street. Katrina Hohowski has an amazing eye for curating and markets a beautiful vintage wear collection,” Ray said. “She has many years of experience, and is as kind as the day is long.” The shop offers a mix of vintage apparel, accessories and handmade items that appeal to both locals and visitors.

When it comes to connecting with nature, Ray recommends Sipp Bay, a scenic coastal preserve off Route 1 in Perry. The trail is described as a long walk rather than a strenuous hike, but its beauty is “invigorating.” “I swear you can feel something powerful in the air and ocean there. It’s drop‑dead gorgeous at sunset, and it is not unusual to spot bald eagles fishing there,” Ray noted. Sipp Bay, located in Cobscook Bay in Perry, is about 10 miles from Eastport and has a rich history as an important hunting and fishing site for the Passamaquoddy people. The preserve’s name is derived from Scipio Dalton, a freed African slave who built a cabin there with his wife in the late 1700s.

For a quiet, historical detour, Ray points to the Tides Institute & Museum of Art, which has rescued many buildings in Eastport from decay. Her favorite is a small child’s playhouse built in the early 1900s, tucked away behind Seamen’s Church on Middle Street. “When I was a child, it was just off the road and my mother and I would always swoon over it when we rode past. I just love that it has been preserved,” she said.

Ray’s commentary is part of a series called “Five Things,” which asks locals to highlight their favorite spots and hidden gems in Maine. The series aims to guide readers in exploring the state town by town. Readers who wish to suggest a future destination can reach out to Maine News Now’s News & Culture Editor, Katherine Lee, at klee@maine-newsnow.com.

While Eastport may have the smallest population of any incorporated city in the state, its community spirit is palpable, from Ray’s boutique and the bike‑repair shop run by her husband to the local cafés, shops and natural preserves that she lovingly describes. Whether you’re a lifelong resident or a curious visitor, Amy Ray’s recommendations showcase the quiet beauty and friendly neighborhoods that make Eastport a unique place to call home.