Directions from Boston, Massachusetts to Brewster, Massachusetts





UpTake Roadtrip Beta

We've selected a few points along the way for you to stop. We are trying to surface things you may not find elsewhere, but if we make some poor choices, please understand. Your feedback is appreciated.


Ashumet Holly Wildlife Sanctuary

Wildlife / Animals – East Falmouth, Massachusetts

Located in East Falmouth, this 49-acre sanctuary of woods, ponds, meadows, hik- ing paths and rare trees is run by the Massachusetts Audobon Society and is a "place of beauty for the tranquility of all. " Ashumet Holly is well known ... More on Falmouthchamber.com

Manomet, Inc.

Museums – White Horse Beach, Massachusetts

Cape Cod Children's Musum

Museums – New Seabury, Massachusetts

Crooked River

Things To Do – Wareham, Massachusetts

The Crooked River is a small tributary of the Wareham River located entirely within the town of Wareham, Massachusetts (USA). Its source is found in salt marshes and cranberry bogs east of Indian Neck Road, and its mouth empties into ... More on AnglerWeb.com

Baker Pond

Beaches – Orleans, Massachusetts

Baker Pond is a 26 acre, natural kettlehole pond with a maximum depth of 60 feet and an average depth of 18 feet. Transparency is good, extending to 11 feet or more, but aquatic vegetation is scarce. The shoreline is moderately developed ... More on AnglerWeb.com

Highfield Hall

Things To Do – Falmouth, Massachusetts

Before the Vanderbilt's and the Belmont's had built summer cottages in Newport the Beebe Family had built their summer homes in Falmouth. ... More on igougo

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  • Elegant Queen Ann style mansion originally built for Beebe family of Boston in 1878. This estate now serves as a cultural and historical landmark for residents of Falmouth and ... More on Massvacation.com

Chatham Railroad Museum

Museums – Chatham, Massachusetts

My husband and I checked out this tiny museum (housed at the former train depot in Chatham) on a weekday in July of 2011. Although small, if you have any interest in trains, Cape history, or are ju... More on TripAdvisor

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  • The Chatham Railroad Museum is contained in the beautifully restored 1887 railroad depot that served Chatham residents and visitors for many years. Featuring an architectural style called Railroad... More on Town.chatham.ma.us

  • Even if you're not a railroad fanatic, it's worth visiting this beautiful 1887 depot to imagine the sights that would greet a Victorian visitor. To begin, the building itself is a "Railroad Gothic... More on Frommers

Duck Creeke Tavern

Things To Do – Wellfleet, Massachusetts

This is a place we definitely will go back to. More on TripAdvisor

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  • This is a place we definitely will go back to. More on TripAdvisor

  • My husband & I drove down to Truro one evening (we live in the mid Cape area) and on the way back, stopped ... More on TripAdvisor

Monument Beach

Beaches – Monument Beach, Massachusetts

Monument Beach is not a fantastically visited section of coast, but it is one of many great pieces of coast in this area. This part of Massachusetts is always a delight to pop by all through the summertime months. The campgrounds ... More on GoingOutside

Dunroamin' Trailer Park

Campgrounds – Sandwich, Massachusetts

None Available More on GoCampingAmerica

Papa Gino's

Restaurants – Wareham, Massachusetts

Nora Bella

Restaurants – West Dennis, Massachusetts

Waquoit Bay Nat'l. Estuarine Reserve (SP)

Campgrounds – East Falmouth, Massachusetts

The name of this park is "Waquoit Bay National Estuarine Research Reserve." This reserve covers 2,500 acres of coastal upland, wetland, beach and bay on the southern shore of Cape Cod, in the Towns of Falmouth and Mashpee. Washburn ... More on ReserveAmerica.com