Sheep Pond, Brewster, and Cape Cod Guidebook
Food scene
Casual local spot for breakfast and lunch featuring reliably delicious, healthy food.
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Cafe Alfresco
1097 Main StCasual local spot for breakfast and lunch featuring reliably delicious, healthy food.
The Brewster Fish House
2208 Main StA local favorite specializing in seafood.
Casual dining with good choices in comfort food and local cuisine with associated pub, The Woodshed. Varied menu in historic building.
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Brewster Inn & Chowder House
1933 Main StCasual dining with good choices in comfort food and local cuisine with associated pub, The Woodshed. Varied menu in historic building.
Elegant place for appetizers and wine, lunch or dinner overlooking Cape Cod Bay.
Ocean Edge Beach Bar
Elegant place for appetizers and wine, lunch or dinner overlooking Cape Cod Bay.
Casual outdoor dining offering hot dogs and burgers, fried seafood, ice cream and more - near the beach and state park.
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Cobie's
3260 Main StCasual outdoor dining offering hot dogs and burgers, fried seafood, ice cream and more - near the beach and state park.
Apt Cape Cod
2149 Main StreetFine dining with an interesting menu appealing to foodies.
Lovely setting with exceptional food and attractive, comfortable ambiance in Orleans.
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Mahoney's Atlantic Bar & Grill
28 Main StLovely setting with exceptional food and attractive, comfortable ambiance in Orleans.
Beacon Room
23 West RdReliably good menu and service.
Fine dining in upscale setting in Dennis overlooking Nantucket Sound.
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The Ocean House Restaurant
425 Old Wharf RdFine dining in upscale setting in Dennis overlooking Nantucket Sound.
Upscale spot for appetizers and wine, lunch or dinner overlooking Pleasant Bay. Fire pits, live music.
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Wequassett Resort and Golf Club
2173 MA-28Upscale spot for appetizers and wine, lunch or dinner overlooking Pleasant Bay. Fire pits, live music.
Comfortable, attractive restaurant serving varied menu overlook marsh in Dennis.
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The Marshside
28 Bridge StComfortable, attractive restaurant serving varied menu overlook marsh in Dennis.
Excellent menu served both indoors and out, near the Dennis Playhouse and Cape Cod Museum of Art.
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Encore Bistro and Bar
36 Hope LnExcellent menu served both indoors and out, near the Dennis Playhouse and Cape Cod Museum of Art.
Impudent Oyster
15 Chatham Bars AveA local Chatham favorite for seafood prepared to perfection.
Perhaps the finest dining on Cape Cod, located in an historic building and affiliated with a Bistro equally fine.
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Chillingsworth Restaurant
2449 Main StPerhaps the finest dining on Cape Cod, located in an historic building and affiliated with a Bistro equally fine.
Elegant setting, elegant food, elegant service overlooking Pleasant Bay in Chathm.
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Chatham Bars Inn
297 Shore RdElegant setting, elegant food, elegant service overlooking Pleasant Bay in Chathm.
If you're venturing out to Provincetown, Napi's offers the funkiest setting - and some of the best food - there.
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Napi's Restaurant
7 Freeman StIf you're venturing out to Provincetown, Napi's offers the funkiest setting - and some of the best food - there.
If you're looking for lobster or anything seafood, and you want views of P-town harbor, this crowded, lively spot should fill the bill.
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The Lobster Pot
321 Commercial StIf you're looking for lobster or anything seafood, and you want views of P-town harbor, this crowded, lively spot should fill the bill.
Scargo Cafe
799 Main StLoads of menus choices, casual and friendly environment.
A casual cafe on the harbor with everyone's favorite seafood. Dining is outside on picnic tables.
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Sesuit Harbor Cafe
357 Sesuit Neck RdA casual cafe on the harbor with everyone's favorite seafood. Dining is outside on picnic tables.
Amazing vegetarian, vegan, and gluten free menu for casual outdoor dining or take out.
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Karma Foods
2628 Main StAmazing vegetarian, vegan, and gluten free menu for casual outdoor dining or take out.
Neighborhoods
Known as The Sea Captain's Town, Brewster is a small village located on Old King's Highway, one of the most beautiful scenic drives in the country. There are eight public beaches on Cape Cod Bay...and Brewster features the largest area of tidal flat on the east coast. The main street is lined with the historic homes of sea captains, who knew that houses were safest located away from the waterfront.
There are vast areas of conservation land, including Nickerson State Park, the Punkhorn Parklands, Drummer Boy Park overlooking Cape Cod Bay, and The Brewster Museum of Natural History. There are over 40 freshwater ponds, many with public landings. The Cape Cod Rail Trail Bike Path passes through the town, and it's easy to rent bikes and cycle as far as Dennis or Wellfleet.
The town is dotted with restaurants, galleries, museums, and a plethora of lovely hiking trails. There's little commerical development here, though you'll find what you want in the small markets here -- or in larger stores in adjoining villages closeby.
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Brewster
Known as The Sea Captain's Town, Brewster is a small village located on Old King's Highway, one of the most beautiful scenic drives in the country. There are eight public beaches on Cape Cod Bay...and Brewster features the largest area of tidal flat on the east coast. The main street is lined with the historic homes of sea captains, who knew that houses were safest located away from the waterfront.
There are vast areas of conservation land, including Nickerson State Park, the Punkhorn Parklands, Drummer Boy Park overlooking Cape Cod Bay, and The Brewster Museum of Natural History. There are over 40 freshwater ponds, many with public landings. The Cape Cod Rail Trail Bike Path passes through the town, and it's easy to rent bikes and cycle as far as Dennis or Wellfleet.
The town is dotted with restaurants, galleries, museums, and a plethora of lovely hiking trails. There's little commerical development here, though you'll find what you want in the small markets here -- or in larger stores in adjoining villages closeby.
Arts and Culture
Don't miss extraordinary productions in this local theater blending local talent with professional actors...and also offering outdoor children's theater in a natural setting near the Bayl
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Cape Rep Theatre
3299 Main StDon't miss extraordinary productions in this local theater blending local talent with professional actors...and also offering outdoor children's theater in a natural setting near the Bayl
The Cape Playhouse, named one of the 50 Best Small Stage Theatres in America, is the longest-running professional summer theater in the country. Known as the “Place Where Broadway Goes to Summer” by The New York Times, The Cape Playhouse has attracted a long litany of famous actors since its inception in 1927.
There is currently no news on the 2021 season.
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The Cape Playhouse
820 Main StThe Cape Playhouse, named one of the 50 Best Small Stage Theatres in America, is the longest-running professional summer theater in the country. Known as the “Place Where Broadway Goes to Summer” by The New York Times, The Cape Playhouse has attracted a long litany of famous actors since its inception in 1927.
There is currently no news on the 2021 season.
The Orpheum not only offers thought-provoking film, it also displays the work of local artsts and offers appealing cuisine in its small bistro. During the pandemic it has streamed lectures on local issues such as preserving historic sites on the Cape and analyzing dance. Stay tuned!
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Chatham Orpheum Theater
637 Main StThe Orpheum not only offers thought-provoking film, it also displays the work of local artsts and offers appealing cuisine in its small bistro. During the pandemic it has streamed lectures on local issues such as preserving historic sites on the Cape and analyzing dance. Stay tuned!
Once the Harwich Junior Theater, the Cape Cod Theater Company now offers theater productions throughout the year, as well as classes in all aspects of theater.
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Cape Cod Theatre Company / Harwich Junior Theatre
105 Division StOnce the Harwich Junior Theater, the Cape Cod Theater Company now offers theater productions throughout the year, as well as classes in all aspects of theater.
This museum features the work of local artists on Cape Cod and also offers classes in a variety of artistic endeavors.
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Cape Cod Museum of Art
60 Hope LnThis museum features the work of local artists on Cape Cod and also offers classes in a variety of artistic endeavors.
Theatrical productons featuring Cape Cod actors. Classes in dance, music, and theater.
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Academy of Performing Arts
120 Main StTheatrical productons featuring Cape Cod actors. Classes in dance, music, and theater.
Hailed by The New York Times “A Triumph of Quality”, the Cape Cod Chamber Music Festival has grown to become an established year-round presenter of chamber music and a major contributor to the cultural life of Cape Cod since its inception in 1979.
The 2021 schedule should be announded shortly.
Cape Cod Chamber Music Festival
35a Brittany's WayHailed by The New York Times “A Triumph of Quality”, the Cape Cod Chamber Music Festival has grown to become an established year-round presenter of chamber music and a major contributor to the cultural life of Cape Cod since its inception in 1979.
The 2021 schedule should be announded shortly.
Built in 1930 as a theater, many assume it was originally a church....bolstered by the presence of a remarkable 6400 square foot ceiling mural portraying Rockwell Kent's vision of heaven. The Cape Cinema, a non-profit, brings to Cape Codders and visitors alike art cinema, The Met, National Theater, and the Bolshoi.
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Cape Cinema
35 Hope LnBuilt in 1930 as a theater, many assume it was originally a church....bolstered by the presence of a remarkable 6400 square foot ceiling mural portraying Rockwell Kent's vision of heaven. The Cape Cinema, a non-profit, brings to Cape Codders and visitors alike art cinema, The Met, National Theater, and the Bolshoi.
Sightseeing
Founded in 1961 by President John F. Kennedy, the Cape Cod National Seashore preserves over 43,00 acres of dunes, woodlands, ponds, and 40 miles of the Atlantic shoreline. Within this treasure you can swim, fish, kayak, sail, camp...and connect with the essence of the Cape as Henry David Thoreau discovered so many years ago.
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Cape Cod National Seashore
99 Marconi Site RoadFounded in 1961 by President John F. Kennedy, the Cape Cod National Seashore preserves over 43,00 acres of dunes, woodlands, ponds, and 40 miles of the Atlantic shoreline. Within this treasure you can swim, fish, kayak, sail, camp...and connect with the essence of the Cape as Henry David Thoreau discovered so many years ago.
Rentals of bikes, kayaks, paddleboards...located near the Rail Trail.
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Rail Trail Bike Shop
302 Underpass RdRentals of bikes, kayaks, paddleboards...located near the Rail Trail.
Cruise from Orleans to Chatham past seal colonies with a stop at the Chatham fish pier to check out the catch of the day.
Seal Watch
174 Crowell RdCruise from Orleans to Chatham past seal colonies with a stop at the Chatham fish pier to check out the catch of the day.
An iconic country store dating back to 1852 and originally the First Parish Unitarian church, this is the go-to meeting place for locals. Grab a cup of coffee to sip on the front benches as you visit with your friends, or go next door for an ice cream cone at the Brewster Scoop. Don't forget to feed the player piano a dime for a little antique ambiance.
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The Brewster Store
1935 Main StAn iconic country store dating back to 1852 and originally the First Parish Unitarian church, this is the go-to meeting place for locals. Grab a cup of coffee to sip on the front benches as you visit with your friends, or go next door for an ice cream cone at the Brewster Scoop. Don't forget to feed the player piano a dime for a little antique ambiance.
Said to be among the best courses on Cape Cod, The Captain's Course feature two par-72 courses with 18 holes each.
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The Captains Golf Course
1000 Freemans WaySaid to be among the best courses on Cape Cod, The Captain's Course feature two par-72 courses with 18 holes each.
Here's the best of two worlds: enjoying gorgeous sunsets while enjoying a refreshing drink and delicious lobster roll! It's a great way to end a day!
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Lobster Roll Cruises
357 Sesuit Neck RdHere's the best of two worlds: enjoying gorgeous sunsets while enjoying a refreshing drink and delicious lobster roll! It's a great way to end a day!
Albert Crosby grew up in Brewster, moved to Chicago where he made his fortune in distilling alcohol, and returned to Brewster with his young wife. In 1888 he built this monument to his love for her on the site of his original and modest boyhood home. The mansion features 35 rooms, 15 fireplaces and a 60 foot viewing tower.
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Crosby Mansion
163 Crosby LnAlbert Crosby grew up in Brewster, moved to Chicago where he made his fortune in distilling alcohol, and returned to Brewster with his young wife. In 1888 he built this monument to his love for her on the site of his original and modest boyhood home. The mansion features 35 rooms, 15 fireplaces and a 60 foot viewing tower.
Nature and Parks
Nothing compares to a few hours spent observing the whales of Cape Cod in their natural habitat, learning their behaviors, experiencing the thrill of watching them breech. The owners of the Dolphin Fleet are committed to protecting this gentle giants who share our waters.
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Dolphin Fleet Whale Watch
307 Commercial StNothing compares to a few hours spent observing the whales of Cape Cod in their natural habitat, learning their behaviors, experiencing the thrill of watching them breech. The owners of the Dolphin Fleet are committed to protecting this gentle giants who share our waters.
A lovely 1.8 mile trail through marshes, past the beach, over boardwalks, graced iwth wildflowers and butterflies, near the Captain Penniman House, c. 1868. Take the Fort Hill exit off Route 6.
Red Maple Swamp Trail
EAST-26-011A lovely 1.8 mile trail through marshes, past the beach, over boardwalks, graced iwth wildflowers and butterflies, near the Captain Penniman House, c. 1868. Take the Fort Hill exit off Route 6.
Fort hill trail
Adjacent to Red Maple Swamp Trail
A treasure of 835 acres once used by the Saquatucket Tribe for hunting and fishing, this conservation land offers aa wide variety of trails to walk and access to many of Brewster's fresh water ponds. Hint: take a map - it's easy to get lost!
Punkhorn Parklands
A treasure of 835 acres once used by the Saquatucket Tribe for hunting and fishing, this conservation land offers aa wide variety of trails to walk and access to many of Brewster's fresh water ponds. Hint: take a map - it's easy to get lost!
Between 3.9 and 8.8 miles, this is considered the Cape's most challenging trail. It winds through forests, marshes, over dunes, past beaches. Be sure to check the tides before you go or you may end up stranded on the island!
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Great Island Trail
1440 Chequessett Neck RdBetween 3.9 and 8.8 miles, this is considered the Cape's most challenging trail. It winds through forests, marshes, over dunes, past beaches. Be sure to check the tides before you go or you may end up stranded on the island!
A jewel in the heart of Brewster, you'll find a variety of hiking trails (try those around Little Cliff Pond or Cliff Pond), biking trails, picnic areas, and camp sites here.
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Nickerson State Park
3488 Main StreetA jewel in the heart of Brewster, you'll find a variety of hiking trails (try those around Little Cliff Pond or Cliff Pond), biking trails, picnic areas, and camp sites here.
Try walking along Cape Cod Bay from any of the beaches in Brewster: Breakwater and Crosby Landing offer good parking, which requires a sticker before 5pm. An interesting variation is going at low tide, which opens up an entirely different world to strollers.
Cape Cod Bay
Try walking along Cape Cod Bay from any of the beaches in Brewster: Breakwater and Crosby Landing offer good parking, which requires a sticker before 5pm. An interesting variation is going at low tide, which opens up an entirely different world to strollers.
A wonderful introduction to the seashore,, its natural treasures and history.
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Cape Cod National Seashore Salt Pond Visitor Center
50 Nauset RdA wonderful introduction to the seashore,, its natural treasures and history.
A wonderful presentation of natural life on the Cape, with lots of hands-on exhibits for kids. There are guided hikes and classes, and a walking trails. Don't miss the nesting ospreys.
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Cape Cod Museum of Natural History
869 Main StreetA wonderful presentation of natural life on the Cape, with lots of hands-on exhibits for kids. There are guided hikes and classes, and a walking trails. Don't miss the nesting ospreys.
Visit the windmill, march around the gazebo during Sunday night bandstand concerts, or just spread a blanket, bring a picnic, and relax at the views of the Bay.
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Drummer Boy Park
773 Main StVisit the windmill, march around the gazebo during Sunday night bandstand concerts, or just spread a blanket, bring a picnic, and relax at the views of the Bay.