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Worcester Street passes over Stillwater River, giving a fantastic view across the water to the Old Stone Church. It was built in 1891 and is listed on the National Register of Historic Places.

Prospect Hill Road to Fruitlands is a local favorite segment of riding. As you climb up the road, you get increasingly open views out to Mount Wassuchet (the tallest mountain in the state) over a historic stone wall. In the fall, when the leaves are changing colors, it is a truly stunning view. Just past the summit of the hill is the turn off for the Fruitlands Museum. Fruitlands was a short-lived utopian community started in the 1840s by Amos Bronson Alcott, Louisa May Alcott's father, and Charles Lane. Today it is a museum and also once hosted a amateur cyclocross race from 2015-2019. It quickly became a local favorite race due to its difficult course over rough and muddy surfaces.

This is a really nice view out over the Eastview Conservation Land as you roll in or out of Harvard Center. This is a pretty section of riding through the woods; be sure to keep an eye out for animals and bird as you pedal past.

The Harvard General Store is a beloved local institution. Sitting right on the edge of the town square, this general store is an amazing place to begin or end a ride. It's a great place to grab a coffee, sandwich, or pastry with indoor and outdoor seating.

when the main road is closed in the spring for debris/snow removal, you can take north road to get to the summit, it is gravel but doable on a road bike.

Upper Westboro Reservoir is part of the Westboro Reservoir & Conservation Land. The lake is a peaceful place, surrounded with grassy areas and woodlands, providing a nice place for picnicking, fishing or simply enjoying a nice bike ride through the trail system that goes around the water.

There is a bit of everything here at Louisa Lake. It is a very scenic area and along with nearby Milford Pond, it provides a great venue for a variety of recreational activities, especially bicycling. Nearby is the Upper Charles Trail, a super good cycling trail.

State park on the banks of the Lake Quinsigamond. There are 2 sites for the park and this site has picnic areas with grills, restrooms and a beach where you can swim in the lake.