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The Castine Town Common is the heart of the historic district of the small seaside town of Castine. There are several historic buildings that surround the Town Common including the Unitarian Universalist Church, which was founded in 1790. The Maine Maritime Academy is also just a few blocks from here along with the Castine Post Office, which is one of the oldest Post Office buildings in continuous operation in the United States.

Harriman Pond is a small freshwater pond near Dedham, Maine. This pond has no public access but it is nice to look out for birds, deer, and other wildlife as you ride past.

Hancock Pond is a pretty freshwater pond east of Bucksport and south of Bangor, Maine. This is a nice spot to keep an eye out for birds and other wildlife as well as kayakers in the spring and summer.

The Michael Michaud Trail is a multi-use trail that passes through downtown Millinocket and a handful of the city's parks. The path follows along with the main stream running through the middle of town, and it even passes by some of the stores and restaurants in the city.

Hannibal Hamlin Parkway is a small park on an island in the middle of Bangor, Maine. This unique park, surrounded by the Kenduskeag Stream has old canons, city views, and a statue of Hannibal Hamlin, an American diplomat who came from Bangor.

Orono sits just south of Old Town, Maine, on the Penobscot River. This small town was named for Chief Joseph Orono, a sachem of the Penobscot Nation, whose people have long occupied these lands. It is home to the University of Maine, the state's flagship institution. In large part because of the student population, Orono is full of fun cafes, shops, and restaurants, and is a nice place to stop as you ride around the area.

Old Town, Maine, sits between the Stillwater River to the west and the Penobscot River to the east. This small town is a great place to stop for a mid-, or post, ride bite to eat at one of the many local restaurants and cafes.

Winterport is located along the Penobscot River and once was home to many sea captains who built homes along Main Street. Today, these remaining homes make up the Winterport Historic District, which is listed in the National Register of Historic Places. For visitors, Winterport offers a number of charming restaurants and cafes near the river.