Destinations

Where the tour takes you.

A scenic walk along Shore Road and through town — stories, savory tastings, and stops at our local partners and friends.

Book Now
Cape Cod’s only walking food tour

A taste of the real Chatham.

We begin with a scenic walk along Shore Road before weaving through town and visiting several of our local partners and friends along the way. Throughout the tour, guests stop at notable historic locations while learning about Chatham’s rich maritime history, culture, and present-day character.

Location
Chatham, Massachusetts
Best Time to Visit
May – October
Languages Spoken
English
What to expect

Discover Chatham, one bite at a time.

Every tour includes

  • 3 savory tastings
  • 1 alcoholic beverage or soft drink
  • Dessert
  • Guided storytelling focused on local history, culture, and landmarks
  • A relaxed walking experience through some of Chatham’s most picturesque areas

Optional drink packages and pay-as-you-like add-ons are available at any stop, time permitting.

Perfect for

  • Seafood lovers and non-seafood eaters alike
  • Couples, families, and small groups
  • Guests looking for authentic Cape Cod experiences

Fun. Local. Delicious.

Book Now
Featured Stops

On the Chatham Food Tour.

  • Hand-picked local restaurants, markets, and sweet spots
  • A mix of iconic Cape Cod favorites and hidden gems
  • Fresh flavors inspired by Chatham’s coastal heritage
  • Tastings featuring seasonal ingredients and local pride
  • Stories about the food, the people, and the town’s history
  • A unique experience — no two tours are exactly alike
  • Small-town Cape Cod hospitality at every stop
  • Flavor, history, and fun woven into one unforgettable walk
Chatham Pier Fish Market
Our Friends at

Chatham Pier Fish Market

Fresh local seafood, tasty alternatives, and authentic Cape Cod flavors served in a lively, family-friendly setting.

Don’t miss The freshest seafood on Cape Cod.
Book Now
Chatham Bars Inn
Our Friends at

Chatham Bars Inn

Discover the charm of Chatham Bars Inn.

Don’t miss Fresh seasonal offerings inspired by the Inn’s nearby farm and Cape Cod waters.
Book Now
Tropical cocktails at Aplaya Kitchen + Tiki Bar
Our Friends at

Aplaya Kitchen + Tiki Bar

A burst of color tucked between Chatham’s historic streets. Tiki-style vibes, vibrant plates, and one of the most photogenic stops on the tour. The kind of place that surprises every guest in the best way.

Don’t miss Authentic Filipino dishes and a Mai Tai you’ll remember.
Book Now
At the Wild Goose Tavern
Our Friends at

Wild Goose Tavern

Chatham’s beloved Main Street tavern — warm, low-ceilinged, full of locals. This is the stop where the pace slows down, the conversation deepens, and the comfort food does its work.

Don’t miss Tavern hospitality the way locals know it.
Book Now
Buffy’s Ice Cream Café
Our Friends at

Buffy’s Ice Cream Café

The home of Chatham Ice Cream Bars, handcrafted frozen treats, and classic Cape Cod summer flavors.

Don’t miss Home of the Chatham Ice Cream Bars.
Book Now
The Chatham Squire at golden hour
Our Friends at

The Chatham Squire

An iconic Main Street pub known for its lively atmosphere, local flavor, and decades of Cape Cod tradition. A stop that feels unmistakably Chatham.

Don’t miss The pulse of Main Street, on a plate.
Book Now
Inside the Chatham Cookware Cafe
Our Friends at

Chatham Cookware Cafe

Your favorite neighborhood cafe, nestled in the center of Chatham, Cape Cod. Delicious sandwiches, strong coffee, and sweet treats — what more could you need?

Don’t miss Cape Cod’s coziest counter coffee.
Book Now
About the stops

Destination questions.

The most-asked questions about the route, the stops, and what to expect.

How are the tour stops selected?

Each stop is hand-picked by Mike for its quality, authenticity, and connection to Chatham’s food scene. We work only with locally owned businesses that offer a true taste of Cape Cod.

Will I get to meet the chefs or owners?

Often, yes. Many of the owners and chefs come out to greet our groups and share the story behind their dishes. It’s one of the best parts of the experience.

How many stops are included?

Tours include 4–5 tasting stops over three hours. The exact lineup may rotate based on the season and partner availability — but every tour follows the same hand-picked Chatham route.

Are all the destinations within walking distance?

Yes — the entire tour covers about one mile of relaxed walking through downtown Chatham. We move at an easy pace with plenty of stops to rest and enjoy.

Can I revisit any of the spots after the tour?

Absolutely. Many guests return to their favorite stop later that day or the next morning. Mike will share his recommendations for what to come back for.

Ready to taste it?

Pick a date and we’ll see you on Main Street.

Book your tour