Our family enjoyed a relaxing trip to Boothbay Harbor, Maine. Boothbay is just over an hour northeast from Portland. It offers a seaside escape with a wide range of restaurants, gift shops, and art galleries. This village is set against the backdrop of a picturesque ocean front working port. The homes are quaint with lush gardens, small rolling hills, and the town feels cozy and approachable. We found street meter parking but these are more limited on holiday weekends. There are many small local side trips that fill a few days to a week. The footbridge offers quaint water views, perfect for family selfies. There are plenty of options for a romantic weekend away as well. Importantly, there is something here for every budget.
Below are some of our highlights from the trip:
Start your day off with breakfast at any of the small locally owned cafes.
For s sweet treat, we especially liked Mama D’s coffee and walnut coffee cake. They also serve scones and muffins, great for taking along for later in your adventure. This felt like a secret local’s place. We stumbled upon it just outside the main tourist area of town. It is walkable from the footbridge. The interior is cozy, like Grandma’s house. They offer a full breakfast menu with legendary breakfast sandwiches. They have a parking lot (free for customers). There is a cute outdoor patio on the backside of the house. If alone, there are a few seats at the small breakfast bar to grab a coffee while you plot your day. Cash or check only. https://www.mamadscafe.net/
For picturesque views of the harbor and enclosed patio seating, try Harborside 1901 grill. A bit more upscale, we went here without the kids. We had a delicious brunch date overlooking the footbridge. Food was well seasoned with some interesting options like shakshuka, pictured below. They also serve lunch and dinner. https://harborside1901.com/
Breakfast on the deck of the iconic Mine Oyster overlooking the water is family friendly. My omelet was quite good, service friendly. On weekend nights it has live music, often with a dance club vibe. You’ll find locals and tourists, young and old here enjoying the summer together. https://www.mineoyster.net/
Get out on the water
Everyone knows the best island trip is to Monhegan. It is known for its soaring cliffs and epic beauty. It also has well managed trails and famous artist colonies. There are daily trips from Boothbay to Monhegan, about 1.5 hours each way. If you go, be sure to plan your hiking carefully as the trips back to shore are limited.
There are also a few places that offer paddle board rentals, and sea kayak rental and tours. We are a family with 3 young kids. This is not yet a choice for us as only 1 or 2 can fit in a kayak. We will definitely try this in the future when the kids are a bit older.
Additionally, there are whale watching and puffin tours, that range in length and availability. be sure to check ahead for departure times.
Scenic 1 hour boat ride to Squirrel Island
If you are looking for something a little less adventurous and time consuming, or are not sure if everyone in your family can handle long boat rides, consider the boat tour of the harbor and Squirrel Island. This mailboat tour leaves multiple times a day on the weekends. There is a roof deck seating and also indoor lower deck seating. The ride was smooth and the Captain narrates the tour, pointing out local landmarks and history. If you are lucky you even see the osprey on their harbor nesting posts! It was perfect time on the water for our small kids.
Views of lighthouse and osprey nest from boat
Explore the beaches, preserves, and trails
Southport Island – Hendrick’s Head Trail and Kitten Island
A short drive across a small bridge takes you to sleepy and quaint Southport Island
Get some steps in. Hendrick’s Head Trail is a very short easy wooded nature trail, managed by the Boothbay Region Land Trust. It is just a few steps away from the public beach. Park and walk back up the road you came in on. The trail meanders about 0.5 miles. It has a loop at the end, through a pine forest with lush and interesting moss and lichens on the ground. The trail has minimal elevation gain.
After your short hike, head over to the beach for calm shallow wading waters and the prominent Kitten Island. During low tide, you can climb up on it. We brought out a picnic lunch and lounged in the sun on top.
It also offers excellent views of the Hendrick’s head lighthouse. The lighthouse is privately owned and inaccessible to the public, but serves as an impressive backdrop for photos.
East Boothbay Scenic Drive
It is worth a drive to Ocean Point at the tip of East Boothbay Harbor. You’ll see quaint cottages, rocky shorelines, small islands, and peaceful sailboats in the Bay.
Barrett’s Park
This cute park is a short distance from downtown, off Lobster Cove Road. Here you will find a waterfront shaded area with benches. The kids enjoyed skipping stones and swinging from the old fashioned tree swing. The water is calm and good for wading.
Coastal Maine Botanical Gardens
This legendary New England garden is worth an afternoon. The main central gardens would take a leisurely 2 hours to explore. But the outer gardens are worth extra time as well. We kept our kids occupied searching the the next Giant Troll, scattered throughout the park. https://www.mainegardens.org/
Shopping
Spend time in this wonderful little shop, Mung Bean, full of items made in Maine and USA. It’s never too early to Christmas shop for pottery, ornaments, glass blown pumpkins. The staff is knowledgeable and can tell you about a lot of the Maine artists that sell their work there. /http://mungbeanmaine.com/
Just down the road grab a bag of Maine made gourmet popcorn at the flagship Coastal Maine Popcorn Company store. Kids especially love the maple flavored popcorn, but I love the savory kinds like salt and vinegar and dill pickle. Grab a bag for yourself and another for an office souvenir. /https://www.coastalmainepopcorn.com/
Head towards the downtown boat launch. You will find innumerable small gift and artisan shops. There are also multiple opportunities to buy that sweatshirt you forgot to bring along.
Galleries
Studio 53 is set in a cute 3 story vintage home. It is part owned by Terry Seaman, one of the experienced artists that also shows his work there. You will often find him on the porch chatting with passerby. His interesting art is inspired by subatomic particles, and there is also a variety of other art within. https://www.boothbayharbor.com/shop/studio-53/
Gleason Fine Art Gallery showcases some beautiful high end original art pieces. https://www.gleasonfineart.com/
Richard MacDonald Stained Glass is a little off the beaten path but so worth the trip. He is often in his shop and eager to share his decades of experience in creating fine glass pieces. The front room, porch, and garden display his plethora of hand made stained glass items. You’ll find trinkets, lamps, mirrors, and full window pieces. Even with kids, we spent an hour speaking with him and choosing some small pieces to bring home. He also creates custom orders as well. https://www.rjmglassart.com/
More restaurant options
Marcel’s Submarine Shop
Grab a footlong sub to go on fresh made bread. The Italian Walking Stick is our favorite. Small kids can split one. They are made to order. https://marcelssubshop.com/
Whale’s Tale
https://www.carouselmarina.com/whales-tale-menu
Our family of 5 rented a last minute condo near a working dock/marina and the Whale’s Tale restaurant. The sunset over the marina was spectacular. The restaurant features casual dress with indoor or outdoor seating available on the dock. An agreeable children’s menu is available. They offer refreshing and interesting mixed drinks. The Whale’s Tale has live music on some weekend nights. Our waiter was spectacular. Call ahead for hours. They do take reservations but there were many walk ins while we were there.
I hope this blog was useful in helping you plan your trip to Boothbay Harbor! Love hearing about your own adventures. Email me your tips at:
kit@astrayfish.com
Unless otherwise stated, all photos throughout this blog are my own and cannot be printed or distributed without my permission.
Astray Fish 
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