MomSkoop
Massachusetts coastline offers more than just beautiful ocean views and fresh seafood. Many restaurants along the shore sit in buildings that have witnessed centuries of American history, from colonial times to the present day. These special dining spots let you enjoy delicious meals while surrounded by stories of the past and stunning water views that have inspired visitors for generations.
1. Beach House Grill at Chatham Bars Inn (Chatham, Cape Cod)
Perched on a bluff overlooking Pleasant Bay, this elegant restaurant has been welcoming guests since 1914. The original inn served as a hunting and fishing retreat for wealthy Boston families.
Today’s menu features locally caught striped bass and lobster rolls that taste even better with ocean breezes. Large windows frame spectacular sunsets that paint the sky in brilliant oranges and pinks.
Historic photographs line the walls, showing how little this pristine coastline has changed over the decades. Reservations fill up quickly during summer months.
2. Sesuit Harbor Café (Dennis, Cape Cod)
Morning fog often rolls across this working harbor where fishing boats have docked for over 200 years. Local fishermen still bring their daily catch to nearby docks, just as their great-grandfathers did.
Blueberry pancakes and lobster benedict draw early risers to waterfront tables. The casual atmosphere feels like stepping into a neighbor’s kitchen, complete with friendly waitresses who know regular customers by name.
Weathered pilings and old fishing nets create an authentic maritime setting. This hidden gem stays busy with locals who appreciate honest food and reasonable prices year-round.
3. The Ocean House (Dennis Port, Cape Cod)
Built in 1890 as a Victorian boarding house, this charming restaurant overlooks Nantucket Sound from its wraparound porch. Original hardwood floors creak pleasantly underfoot, telling stories of countless summer visitors.
Fried clams and fish tacos taste perfect while watching sailboats glide across the horizon. The building survived the famous Hurricane of 1938 that destroyed many coastal structures.
Antique nautical maps and vintage postcards decorate the dining rooms. Evening meals on the porch feel magical as lighthouse beams sweep across darkening waters in the distance.
4. Mac’s on the Pier (Wellfleet, Cape Cod)
Raw bars don’t get more authentic than this weathered shack built directly over Wellfleet Harbor. Oyster shells have been piling up beneath these docks since the 1800s, when this area supplied shellfish to Boston markets.
Famous Wellfleet oysters arrive at your table within hours of being harvested from nearby beds. Seagulls hover hopefully while you crack shells and sip cold beer.
High tide brings water right up to the restaurant’s foundation, creating the feeling of dining aboard a ship. Summer crowds don’t mind waiting for tables with such spectacular harbor views.
5. Skipper Chowder House (Yarmouth, Cape Cod)
Clam chowder recipes here date back four generations to when Portuguese fishermen first settled along this stretch of coast. The same family has been serving bowls of creamy goodness since 1946.
Thick chowder loaded with tender clams warms you up on foggy Cape Cod evenings. Knotty pine walls display old fishing photos and nautical artifacts collected over decades.
Picture windows face Lewis Bay, where working boats still head out before dawn. Local families consider this their special place for birthday dinners and anniversary celebrations throughout the year.
6. 71° West Atlantic Steakhouse (Plymouth)
Plymouth Harbor witnessed the Mayflower’s arrival in 1620, making this one of America’s most historically significant dining locations. The restaurant sits near where Pilgrims first stepped ashore to establish their colony.
Prime steaks and fresh lobster complement views of Plymouth Rock and the harbor beyond. Modern cuisine meets colonial history in this upscale waterfront setting.
Replica tall ships often dock nearby during summer festivals, recreating scenes from centuries past. The combination of excellent food and profound historical significance creates unforgettable dining experiences for visitors exploring America’s birthplace.
7. 28 Atlantic at Wequassett Resort (Harwich, Cape Cod)
Spectacular sunsets over Pleasant Bay have been drawing visitors to this scenic point since Native Americans first camped here centuries ago. The resort property includes buildings dating to the 1740s.
Award-winning cuisine features locally sourced ingredients prepared with French techniques. Floor-to-ceiling windows showcase ever-changing water views throughout your meal.
Historic Cape Cod architecture blends seamlessly with modern luxury amenities. Reservations at this AAA Four Diamond restaurant book months in advance, especially for window tables during peak foliage season when autumn colors reflect in the bay waters.
8. C.K. Pearl (Essex, North Shore)
Essex has been famous for shipbuilding since the 1600s, when wooden vessels constructed here sailed to ports around the world. This converted boat building facility still echoes with maritime history.
Fried clams were actually invented in this town, making every order a taste of culinary history. Large portions of perfectly battered shellfish arrive golden brown and steaming hot.
Original wooden beams and nautical artifacts remind diners of the building’s seafaring past. The Essex River flows just outside, where centuries of boat launches once celebrated new vessels heading out to sea for the first time.
9. Yella on the Water (Gloucester, North Shore)
Gloucester’s fishing fleet has been bringing in daily catches for over 400 years, inspiring countless artists and writers. This waterfront spot offers front-row seats to America’s oldest continuously operating fishing port.
Fresh haddock and scallops arrive straight from boats you can see from your table. The casual atmosphere welcomes families and fishing crews alike.
Colorful buoys and weathered rope create an authentic fishing village atmosphere. Storm stories shared by local fishermen add entertainment to your meal while you watch working boats navigate the historic harbor that inspired movies and novels.
10. Warren’s Harborview (Wareham, South Shore)
Buzzards Bay has welcomed sailors and fishermen since before European settlement, when Wampanoag tribes gathered shellfish from these productive waters. The restaurant building dates to the early 1900s.
Stuffed quahogs and fish and chips taste even better while watching boats navigate the busy harbor. Friendly service and reasonable prices keep local families coming back for generations.
Sunset views across the bay create perfect endings to summer days. This family-owned restaurant maintains the welcoming atmosphere of a neighborhood gathering place where everyone feels at home regardless of whether they arrived by land or sea.