A Warm Maine Welcome Awaits

Whether passing through or staying a while, attending a special event, or on vacation to get away from it all, you’ll find a warm welcome waiting for you at our mid-coast Maine hilltop inn. Our goal is for all guests – whether visiting for the first time or returning again – to feel that they’ve arrived at their favorite seaside getaway. We fondly remember childhood visits to a special place that was eagerly anticipated each summer, and look forward to welcoming you to our place!

Location, Location, Location!

The most common question we are asked is “how close are you to town?”. The answer is, we are in the center of Boothbay Harbor, just steps from our main street and waterfront, but on a quiet hilltop. Our unique location, at the highest point in the harbor with over four private acres, offers stunning views while providing our guests with a quiet retreat.

Common Spaces

Chrome Beer TowerThat are anything but common… In the Main House, all guests are welcome to lounge by the living room fireplace with a book or magazine, browse local restaurant menus, or plan your next adventure. BAR ONE will be opening spring 2021. This posh new bar provides an intimate place for guests to gather for a drink or bite to eat before heading out to dinner. Feel free to place your order from the comfort of your Adirondack chair or bistro tables on the front porch and enjoy your beverage on the expansive lawn overlooking the harbor.

We can help with your questions, provide directions and advice for excursions, and make whatever arrangements you need. After breakfast, the nearby dining room is ready with ice, bar ware, snacks, and the hot water kettle for tea, coffee, or hot chocolate at any hour. Cookies, brownies, or other treats appear on most afternoons.

Delicious Full Breakfast Every Morning

Topside Inn BreakfastBreakfast at the Topside Inn is an event, and a major part of what makes a stay at our Inn so unique and special. A delicious gourmet breakfast is always included each morning of your stay at Topside Inn. Enjoy a hot entree special served from the kitchen that is guaranteed to satisfy every taste-bud. Included with the breakfast entree is a full array of continental offerings including Maine-roasted coffee or tea, milk, fresh fruit, homemade granola, yogurt, baked goods, homemade jams and preserves, fresh whipped butter and juices, cereals and much more. Breakfast is the perfect opportunity for our guests to taste the incredible locally-sourced food, fish, and ingredients. For more information, visit our Breakfast page.

The Property

Topside Inn is situated on more than four acres of land, with the Main House fronting McKown Street as it winds tightly up the hill from the center of town. The front lawn, anchored with a row of classic white Adirondack chairs, slopes gently toward views of the outer harbor. The lawn and buildings are bordered by a variety of gardens that are a colorful, continual work in progress. Rooms in the two guesthouses include direct access to covered porch space for taking in the views, and the sweeping front porch on the Main House offers seating for all to enjoy. On summer afternoons a spirited game of croquet or bocce may erupt on the front lawn.

Your Innkeepers

Topside OwnersHello from the owners of the Topside Inn, Mark Osborn and Brian “Buzz” Makarewicz. We are very happy to announce we were just named “Innkeepers of the Year” for 2020 by Hospitality Maine, (Maine’s only non-profit trade group representing the hospitality industry in the state). From the time we got together (and got married in 2013) we knew we wanted to acquire an inn somewhere in the world. Little did we know we would end up buying the inn that we had watched our friends begin to lovingly transform into the perfect haven on the hill. Mark, a fourth generation summer resident of Boothbay, left his corporate life in 2003 and moved to BBH when he bought the Thistle Inn. He sold the inn in 2006 and became the General Manager of Linekin Bay Resort. Buzz bought a house and began vacationing in BBH in 2007 and fell in love with the town. Buzz has his bachelor’s degree from UMass Amherst in Hotel Management and though his career has moved him into Wellness and Technology, he was very excited to get back into hospitality.

As the saying goes, choose a job that you love and you will never work a day in your life. Well we love what we do and we are confident that our passion and dedication will ensure that you will have a wonderful and memorable stay in Boothbay Harbor. – Mark & Buzz

General Manager

In July 2020, Rebekah Messer (Bekah) joined the Topside family. With a diverse and accomplished career in hospitality, most recently managing the Portland Event Center for Cellardoor Winery, Rebekah has enabled us to elevate our level of service even higher and expand our guest amenities, including managing the new in-room wine selections and our new bar. She shares our love of food and entertaining and attended culinary school in Switzerland. For our guests who were able to stay with us since Rebekah has joined us, you know how fortunate we are to have her working with us at Topside. Rebekah’s sister Kim Villard, along with Kim’s husband Philipe, own Villard Studios here in Boothbay Harbor and Rebekah’s family has summered here for many years, so she is very familiar with all our region has to offer and is here to help you plan your perfect Maine vacation.

Our Charitable Giving, Locally, Across the US and Internationally

Along with being proud owners of the Topside Inn, we and our team always try to find ways to give back to our wonderful Boothbay Harbor community and beyond. We currently support a number of local charitable organizations including Coastal Maine Botanical Gardens, Boothbay Region Land Trust, Food for Thought, our local Food Pantry, Chewonki Foundation, and Habitat for Humanity. We are so happy to be a part of such a great community, and we always want to do what we can to support it.

We also donate stays through OneSpareVacation to a number of organizations, the growing list includes Mikey’s Way Foundation, Kids N Hope Foundation, Channel 3 Kids camp, Ray of Light Farm, Women’s Fund of Rhode Island, Project Green Schools, Syracuse Stage and we support worldwide efforts to improve the quality of life for people in need, including the charity started by a couple here in Boothbay helping children in Thailand, Friends of Thai Daughters.

A note on rate discounts. As an organization, we have decided to support children and families in need as well as a number of charitable organizations doing great things to make our world a better place through direct donations and contributions; we do this in lieu of offering discounts on stays at the inn. We feel this is the best way to help the most people in need as equitably as possible. Our goal is to contribute at least 5% of our annual revenues to these worthy causes. We hope that every guest staying at Topside knows they are making the world a little bit better for so many people.

CREDO: A statement of the beliefs or aims which guides one’s actions.

TOPSIDE CREDO: The Three Pillars of Who We Strive To Be.


To provide our guests with an exceptional and authentic Maine coast experience, consistently exceeding expectations for immaculate, well-appointed accommodations, locally sourced ‘over the top’ cuisine and warm, friendly and professional service.


Build and support a fantastic team who love what they do.  Support local farmers, fishermen and businesses who share our community-based goals.  Be proactive members of our community, supporting initiatives related to food insecurity and work to educate and inspire people to raise their own food.


Be a good steward of our planet by reducing our carbon footprint, investing in renewable energy, recycling & composting, increasing our community’s connection with locally grown and raised food and creating a habitat to support local wildlife and pollinators.