Cape Cod is known for its laid back summer vacation spots, beaches, fresh caught seafood, and rich history.  These intertwining pieces are what makes the Cape so special and a place people want to visit over and over. What sets these restaurants apart? Well, you will not only get delicious food and great service, but a story to go with it.

Some of these restaurants including the Old Yarmouth Inn and Whitman House have been welcoming visitors for over 100 years! Others are historic for their presence in the community and location. If the Squires walls could actually talk, the tales it would tell.  

These restaurants have stood the test of time in an ever-changing climate and they each have something unique to offer. If you are visiting the Cape checking out these restaurants is a MUST! 

Originally Published: May 13, 2021

Historic Restaurants on Cape Cod 

Lobster Pot (Provincetown)

Established in 1937 The Lobster Pot is a Provincetown Tradition and the iconic neon lobster sign has guided generations of guests to their door. People come from around the world to experience their fresh seafood, an amazing view of Provincetown Harbor and outstanding Cape Cod hospitality!

Chatham Squire (Chatham)

Established in 1968 Squire has become an iconic staple in the Cape Cod restaurant/bar scene.  It offers a diverse menu in a fun, laid back family friendly atmosphere.  There are license plates and memorabilia all over the walls, which creates a down-home historic feel.

Land Ho (Orleans)

Established in the early 70s the Land Ho! in Orleans is a genuine Cape Cod hang out, with a charm and character all its own. The atmosphere is warm and inviting. Orleans business signs hang from every available ceiling space, reflecting the Ho’s close connection to the local community.

Wicked Oyster (Wellfleet)

The Wicked Oyster was established in 2004. The original structure houses their main dining room and it dates back to 1750. While adding their own touch to the building they are careful to honor its rich history and keep the comfort of a Cape Cod home.

Landfall (Falmouth)

Established in 1946 Landfall Restaurant is a premiere waterfront restaurant. Landfall’s dining room is constructed of wood taken from shipwrecks and boards from old buildings. 

Old Yarmouth Inn (Yarmouth)

Originally established in 1696 this is one of the oldest on the list. The inn was originally used as a wayside inn/stage stop. It no longer welcomes overnight guests, but is an amazing place to stop to enjoy a fresh local culinary experience rich in history. 

Red Cottage Restaurant (South Dennis)

Originally built in 1936 by Walter J. Weeman the Red Cottage started as a 2 1/2-room “cottage.” It has been owned by many families since then. It started out as strictly seafood, later becoming a grocery and eventually expanding to the restaurant it is today.   

Wimpy’s (Osterville)

Wimpy’s was established in 1938 as a small hamburger counter. Over the years as Osterville grew in popularity, so did Wimpy’s. After numerous additions Wimpy’s now has over 200 seats and a thriving retail/take-out market.

Ciro and Sal’s (Provincetown)

Ciro & Sal’s was originally founded by Ciriaco Cozzi and Salvatore Del Deo in 1951 as a coffee shop. Today, the restaurant consists of a number of loosely connected dining areas in a romantic brick wine cellar serving italian specialities. 

Skipper Chowder House (South Yarmouth)

The Skipper Restaurant and Chowder House established in 1936, is one of Cape Cod’s oldest waterfront restaurants with the pristine views of Nantucket sound.  

Sagamore Inn (Sagamore)

The original Sagamore Inn was built in 1900. The restaurant has been sold many times since then. It is a local landmark famous since 1963. The menu includes delicious seafood platters, Italian pasta dishes, as well as, “Shirl’s Yankee Pot Roast.” 

The Dolphin Restaurant (Barnstable)

The Dolphin was started 70 years ago by the current owner Nancy Smith’s grandparents and has been a landmark in Barnstable Village ever since.

Whitman House (Truro)

Established in 1894 by the Whitman Family this restaurant has been welcoming visitors for over 100 years. It started as a bed & breakfast and was then turned into a pancake kitchen in 1962 by the Rice Family. It was changed again in the 70s to the Tavern it is today. This one is a must-visit! 

Swan River Fish Market & Restaurant (Dennisport)

A landmark for Cape Cod’s best seafood, Swan River Restaurant and Fish Market have been proudly serving their guests the freshest catch since 1954. Family owned and operated, Swan River specializes in fresh seafood, lobsters, clambakes, raw bar and more.

Gina’s By the Sea (Dennis)

Established in 1938, Gina’s by the Sea is a landmark eighty-seat restaurant. It is best described as casual elegance in an unpretentious setting.

Mayflower Cafe (Provincetown)

During the winter of 1929-1930, the Janoplis brothers built the Mayflower Café. The Mayflower is currently owned and operated by the third generation of Janoplis’ family and offers a diverse menu of seafood and multicultural cuisine. 


Hi, I'm Jen and I love to travel, go to the beach and write about all the places I have visited. I also have a bucket list of places I can't wait to try! I've visited Cape Cod every summer since I was a kid and now enjoy traveling to all great beach destinations! I have worked in the travel industry for all of my career. I love sharing my experiences of different restaurants and places and helping travelers find the best fit for them!

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