Directions from Great Barrington, 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.


Spirit Well Massage & Yoga

Health Club – Chatham, Massachusetts

Chatham Lighthouse Beach Yoga class held every summer morning at 7:30 AM on beautiful Lighthouse Beach in Chatham. Bring a beach towel, sunglasses and ... More on YogaFinder

Lawrence Pond

Parks – Sandwich, Massachusetts

Lawrence Pond is a 138 acre natural kettlehole pond with an average depth of 15 feet and a maximum depth of 27 feet. Transparency is very good, extending to 16 feet, and aquatic vegetation is scarce. The bottom is composed of sand ... More on AnglerWeb.com

Stage Harbor

Beaches – West Chatham, Massachusetts

You might be tempted to shed your shoes for the sandy hike to the lighthouse, but you might want to think twice about it. If your feet aren't pretty tough already, you might develop a good set of b... More on LighthouseFriends.com

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  • Stage Harbor Lighthouse, established in 1880, had a much briefer and perhaps a bit less interesting history than many other beacons on Cape Cod, however, the station's 20th century keepers stand ou... More on LighthouseFriends.com

Townsend Lobster & Seafood

Tours – Provincetown, Massachusetts

Townsend Lobster & Seafood owner, Chris Townsend, runs lobster- catching tours on his fishing boat. Trips2008 ... More on travelandleisure

Players Tavern

Bars – Whitinsville, Massachusetts

3.5
1 source
Average Rating
3.5 out of 5
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3.5
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Flax Pond

National And State Parks – Brewster, Massachusetts

Travel the road to the upper campgrounds in Nickerson State Park and you may think for a moment that you have been magically transported to the Berkshire Hills or the piney woods of the Carolinas. Nowhere in sight are the sand dunes ... More on Mass.gov

Scusset Beach

Beaches – Plymouth, Massachusetts

Take Rte. 3 south to Sagamore rotary, go 3/4 around rotary bearing right, follow to very end. Follow signs. Parking fee:$5.00 ... More on GoingToTheBeach.com

CityStage and Symphony Hall

Things To Do – Springfield, Massachusetts

I am partial to small playhouses that offer an intimate atmosphere, because, in my opinion, physical proximity helps observers to connect with actors, and thus feel a character's true emotions. Luckil ... More on TripAdvisor

Cape Cod Rail Trail

National And State Parks – Brewster, Massachusetts

History Before the first railroad tracks were laid, the Cape was a relatively isolated area, accessible only by packet boat or stagecoach. By 1848, the Old Colony Railroad Company laid tracks that ... More on Mass.gov

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  • The Cape Cod Rail Trail is one of the brilliant success stories in the nationwide rails to trails movement. Opened in 1978 and extended as recently as 1995, this trail follows the former Old Colony... More on LLBean.com

East Brimfield Lake

National And State Parks – Brimfield, Massachusetts

East Brimfield Reservoir is a 420-acre reservoir created by the Corps of Engineers in 1960 by damming the Quinnebaug River in Sturbridge. Although its primary function is flood control in conjunction with the Thames River Basin Flood ... More on AnglerWeb.com

Nauset Harbor

Things To Do – Orleans, Massachusetts

Nauset Harbor is a sheltered inlet of the Atlantic Ocean, on E coast of Cape Cod, bet. Eastham and Orleans. Lighthouse ... More on AnglerWeb.com

Cape Cod Grille

Restaurants – Hyannis, Massachusetts

3.5
1 source
Average Rating
3.5 out of 5
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3.5
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Little Sandwich Shop

Restaurants – Hyannis, Massachusetts

Christos Pizzeria & Seafood

Restaurants – Teaticket, Massachusetts

I said forget it, didn't eat from there, there are too many good people to support. More on CitySearch

3.5
1 review
2 sources
Average Rating
3.5 out of 5
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3.5
1+ reviews
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  • I was going to give the place a try until I called it. The guy was so rude I actually jumped from shock as ... More on CitySearch

Dunkin' Donuts

Donuts – Attleboro, Massachusetts