The Captain’s Watch

Bed and Breakfast and Sail Charter

Cundy’s Harbor, Harpswell, Maine



Perched atop the most elevated bluff on the point, 250 feet from the water, this gracious 1862 landmark home affords long views over an authentic, small, working harbor and beyond to ledges, islands, river and bays. From the octagonal cupola crowning our rooftop, the panoramic vista to the Atlantic is stunning. Sparkling water showered with buoys provides a colorful confetti background for watching lobster boats, sailing vessels, seals and shorebirds. Hidden from those traveling Route 24 to Orr's and Bailey Islands is Cundy's Harbor, a seaside treasure- just ten minutes from U. S. Route 1 -central to the entire Bath and Brunswick, Maine  region!

The Captain's Watch was built during the Civil War as the "Union Hotel". It later flourished as the "Cliff House" and the "Ocean View House". Recognized by the National Register of Historic Places and the Harpswell Heritage Trust, the eight room original section survives as Maine's "oldest known coastal hotel structure". After its heyday, the inn became a stately private residence until its rebirth as a hospitable bed and breakfast. For the history buff, we have inherited an array of intriguing photos and 'stories' from the days when visitors arrived by schooner, steamer or stage. Come share our pride in the restoration of this charming old home.

We invite you to take pleasure in our private peaceful setting with its commanding views. Sense the allure of the picturesque small fishing village and connect to the sea with a captained sail. From inside the house or from on the decks and terraces, savor the rugged beauty of the harbor's cove, cool sea breezes, country garden landscape and the beautiful architecture of this informal hip-roof Greek Revival home. From our hilltop, delight in brilliant sunrises and sunsets and a 'planetarium' night sky.

View of Cundy's Harbor to the Sea from The Captain's Watch


A warm and cozy atmosphere has been created in this elegant yet unpretentious home. Family antiques and collections of old china and quilts are perfect accents for the lovely rooms. Relax, our furniture is comfortable and meant to be enjoyed- from parlor to dining room to our queen and king sized beds. We insure a good night's sleep for even the tallest of guests. Bedrooms all have private baths and overlook the water. Two share access to the enclosed cupola for the ultimate 360 degree view. The second floor Captain´┐Żs Quarters demi-suite is a favorite for a romantic getaway. Along with the common rooms, the demi-suite also includes a working fireplace, TV, and couch to stretch out on, and can accommodate an extra person. Our first floor rooms all have easy access and are convenient to our cheerful guest library/living room.  Each room has something special to offer.

Breakfast is thoughtfully prepared in the sunny kitchen- follow the aroma of coffee brewing at dawn! Scan the shimmering water with boats stirring on moorings- greet the day from our East facing decks. From 8-9 o'clock, pick up a tray to eat outside or we'll serve you in the original paneled dining room. Indulge yourself to a leisurely meal with congenial conversation and tips on 'area musts'. Our gourmet omelets, cinnamon French toast and sour cream blueberry pancakes are favorites most requested by returning guests- delicious!

Click here for more information about accommodations at The Captain's Watch.

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Water View from 
the Dining Room

Cozy Living Area



Your Hosts

Donna Dillman and Ken Brigham have been inn keeping since 1986. A former Dental Hygiene professor, Donna's special interests include gardening, bridge, cooking and off-season sailing aboard Symbion. Ken, a Bowdoin College graduate and retired Psychological Examiner, is an enthusiastic amateur radio operator and sailor (Coast Guard licensed captain). Having five grown children, they now share their home with only a delightful cat and their welcomed guests.

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Area Activities

A short drive from the hustle and bustle, The Captain's Watch is tucked at the leading edge of the 'real' Maine coast and the many attractions of the surrounding islands and peninsulas. Midway between Kennebunkport and Camden- perfect for day tripping. A guest once said, "Here you can experience 'Down East' without an extra two hour drive!"

Outdoor Activities

  • Sail with Ken aboard the 38-foot sloop, Symbion
  • Fish, kayak or bring a canoe (there are two area put-ins)
  • Explore pristine forests or sandy beaches at Popham and Reid State Parks
  • Hike, nature walk or bike


The Arts


  • Browse for art, antiques and fine crafts in nearby towns of Bath, Brunswick and Topsham- the Freeport outlets and L.L. Bean are only 20 minutes away


  • We'll recommend great restaurants- from gourmet to lobster in the rough, we're happy to make your reservations

Refresh and Renew

  • Being both inland and coastal 'Mainers' since the 1940's, we enjoy sharing our knowledge. This is an excellent homeport for exploring the varied mid-coast region. Even guests who have stayed with us for two weeks experienced something new each day.

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A View of Cundy's Harbor

Room Rates

Rates range from $155 to $185 per room, plus tax, based on occupancy, length of stay, and season.

Click here for more information about accommodations at The Captain's Watch.

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While you may secure your reservation with a Visa or MasterCard, payment by check or cash is required. A deposit equal to the first and last night of your stay (room tariff plus tax) is expected within five days to guarantee an advanced reservation. Any balance is payable upon arrival. Please make checks payable to Donna Dillman for the B&B and to Ken Brigham for sailing charters.

Should cancellation be necessary your deposit will be refunded if notice is received 14 days prior to your scheduled arrival. After that time or with an early departure, you are responsible for any part of the reservation that is not rebooked. Refunds will include a $25.00 processing fee.

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Breaking the Morning Mist


Guest Policies

  • Having only five guest accommodations and being off the beaten path, our reservations are very important. It is suggested that reservations be made well in advance and a two night minimum stay may be requested. If rooms remain available however, we love 'spur of the moment' guests.
  • The house has limited space appropriate for children. Prior arrangement is necessary.
  • Being an historic wooden structure, guests may only smoke outside
  • Check in after 2:00 PM, please advise us if you will be arriving after 8:00 PM.
  • Check out by 10:30 AM.
  • Please advise if you have any special needs so we may try to accommodate you.

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Directions to The Captain's Watch

From Brunswick (going North) or Bath (heading South) take US Route 1 to the exit for Rte. 24, Cook's Corner, Brunswick N.A.S., Orr's and Bailey Islands. Go straight through traffic lights (on Rte. 24 South) for 4.5 miles, then left onto road for Cundy's Harbor. Continue on Cundy's Harbor Road for 4.4 miles to top of small rise, see sign for "Captain's Watch" high on right.

The Google Maps program is very helpful. Click here for a map of the area.

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Map of Mid-coast Maine




For Reservations and Inquiries

The Captain's Watch
Bed and Breakfast
and Sail Charter
926 Cundy's Harbor Road
Harpswell, ME 04079


Phone: 207-725-0979 (please leave us a message if there is no answer)

Note: Photographs of Cundy's Harbor courtesy of B. E. Kenney

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The Cupola atop The Captain's Watch from Cundy's Harbor

Harpswell Business Association