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115 N. High St, (Route 302)
Bridgton, ME, 04009, United States
207-647-5301 | 800-797-5301

Meet Your Hosts

Owner of Highland Lake Resort in Maine

The owners of the Highland Lake Resort are Woody Woodward and his wife, Deanna, both natives of Maine. Born in Portland, most of Woody’s childhood was spent in Cumberland (a town even smaller than Bridgton). Woody graduated from the University of Southern Maine, where he got his BA in Criminal Justice and Theatre and took graduate courses in business and counseling. Dee grew up in Gorham, attended Gorham Schools, and also graduated from USM. She received her Masters in Education from Northeastern University.

Over the years, Woody has had a varied career. He started his first business at the age of 17, and incorporated it at 20. During college, he developed his hobby as a magician into a business, and also worked part-time as a deputy sheriff and police officer. It was then, after he had been diagnosed with arthritis that had actually started in his early teens, that Woody started on a winding path which ended here: from the first male family planning counselor in Maine, to the creator and director of a crime prevention program for a police department, to a full-time professional magician, to owner of a promotional marketing and events agency, to CEO of the Arthritis Foundation’s Maine Chapter.

It was his extensive travel as both an entertainer (performing 175 shows per year) and a CEO that convinced Woody that many motels and inns could use a class in “hospitality”. It also gave him a strong understanding of what things are important to travelers, such as cleanliness, comfort, friendly service, and useful amenities.
After 5 years at the helm of the Arthritis Foundation, and after his position was eliminated through a merger of chapters, Woody decided to try his hand at running an inn. He checked out properties in Bethel, Wells, Kennebunkport, and Downeast Maine before deciding upon the former Arey’s Highland Lake Resort in Bridgton. Most of the other places were too dependent upon just one season. And the coastal areas seemed to be too hectic– too “hustle and bustle” — for his tastes. Since Woody’s ideal vacation had always been at a lakefront cottage, he chose this resort to be his home and workplace. He became the owner on July 1, 1997.

In July of 2001, Woody expanded the Resort family when he got married to Dee, a teacher in SAD 61 who has also had extensive experience in both small and large businesses.

Owners of Vacation Resort in Maine

In addition to running the Resort, Woody served 4 terms (12 years) on the Board of Selectmen for the Town of Bridgton (including 2 terms as chair), is president of a private charitable foundation, co-founder of the Bridgton Business Association, past president of the Board of Directors of the Maine Innkeepers Association. He received the Maine Innkeeper of the Year Award in 2012.


Woody is also a Methodist Pastor, assigned to the Cressey Road United Methodist Church in Gorham, Maine.


rosie on table  Guests may see the newest “mascot” at the Resort walking around with Dee or Woody. “Rosie” is a vivacious, friendly Chiweenie puppy. She is part Chihuahua, part dachshund, and all energy! Stop and say “hi!” if you see her, but please don’t try to pick her up. (She loves to petted and to kiss you, but she’s not very fond of being picked up.)