Chatham Food Tours — Hero v2 Preview
Cape Cod’s Only Walking Food Tour

Savor the flavors of Cape Cod.

A 3-hour walking food tour through Chatham, MA — with hand-picked local bites, hidden gems, and the stories only a local can tell.

5.0 / 36 reviews
Travelers’ Choice on TripAdvisor
100% of travelers recommend
Fresh Local Tastings Scenic 1-Mile Walk Small Groups Sweet, Savory & Seafood-Free Options Hidden Gems & Local Stories 3-Hour Guided Experience

In their own words.

Real reviews from past guests · All 5 stars on TripAdvisor.

Tour group dining at the Chatham Bars Inn during the Chatham Food Tour
★★★★★

THE BEST and most enjoyable time we spent on Cape Cod.

Terence L.
Couples · October 2025
via TripAdvisor
Tour guests with handmade ice cream sandwiches from Buffy's
★★★★★

Best eats we had on a food tour. Highly recommend.

Nicole S.
October 2025
via TripAdvisor
Multi-generation tour group at Buffy's Ice Cream Cafe in Chatham
★★★★★

Mike really knocked this out of the park!

Anna B.
Family · August 2025
via TripAdvisor
Read all 36 reviews on TripAdvisor
Moments from past tours

Stepping into Chatham.

Real photos from past guests. Every stop, every plate, every story — this is what awaits.

Tour guests with cocktails on the beachside deck at Chatham Bars Inn
Chatham Bars Inn
Lobster at the Chatham Pier Fish Market
Chatham Pier Fish Market
Tour guests inside The Chatham Squire
The Chatham Squire
At the Wild Goose Tavern
Wild Goose Tavern
Tour group at the iconic Chatham Bars Inn sign
Chatham Bars Inn
Tour guests at the Chatham Bars Inn
Chatham Bars Inn
Tour guests outside Buffy’s Ice Cream Café
Buffy’s Ice Cream Café
Tropical cocktails at Aplaya Kitchen + Tiki Bar
Aplaya Kitchen + Tiki Bar
Guests at Buffy’s Ice Cream Café
Buffy’s Ice Cream Café
Tour group at the Chatham Bars Inn overlook
Chatham Bars Inn
Inside Buffy’s Ice Cream Café — the final tour stop
Buffy’s Ice Cream Café
The walking tour

Get to know the heart of Chatham.

Hand-picked stops over three hours — the places where Chatham locals actually go.

Chatham Pier Fish Market

Chatham Pier Fish Market


Where Cape Cod's morning starts. We gather at the working fishing pier with salt in the air, watching the boats unload the day's catch. It's the kind of place locals know and visitors usually walk right past.

Don't miss The freshest seafood on Cape Cod.
Chatham Bars Inn

Chatham Bars Inn


A landmark waterfront retreat overlooking Chatham Harbor. Guests experience the beauty, history, and coastal charm of this iconic property while learning how its locally sourced, farm-driven philosophy helps shape one of Cape Cod’s premier dining experiences.

Don't miss Fresh seasonal offerings inspired by the Inn’s nearby farm and Cape Cod waters.
Aplaya Kitchen + Tiki Bar

Aplaya Kitchen + Tiki Bar


The hidden gem locals don't always share. A Filipino-Cape Cod fusion tucked just off Main Street — totally unexpected, totally delicious. Most visitors never find it on their own.

Don't miss Authentic Filipino dishes and a Mai Tai you’ll remember.
Wild Goose Tavern

Wild Goose Tavern


A cozy local tavern where the regulars know each other's names. Comfort food, stories on the walls, and a dish people drive across the Cape for.

Don't miss Tavern hospitality the way locals know it.
Buffy's Ice Cream Café storefront sign — the final tour stop

Buffy's Ice Cream Café


The sweet ending we build the whole tour toward. Home of the Chatham Ice Cream Bars — the kind of place that turns first-time visitors into next-day return guests.

Don't miss Home of the Chatham Ice Cream Bars.
The Chatham Squire

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.
Chatham Cookware Cafe

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.
Mike Calogero, founder and guide of Chatham Food Tours
Your founder and guide

Meet Mike.

Hi, I’m Mike — a Cape Cod native and longtime food lover. After years of sharing hidden restaurant gems and storytelling with visiting friends, I realized something: people don’t just want to eat well on vacation — they want to connect with the culture behind every bite. That’s how Chatham Food Tours was born.

This tour is my way of welcoming you into the town I love, through the flavors, faces, and stories that make it special.

Mike Calogero Founder and Guide

“Mike made us feel like old friends.”

JustJanetperiod · via TripAdvisor
Questions before you book? Mike answers his own phone. (508) 685-8158
Booking

Three steps to your tour.

Easier than picking a restaurant for dinner.

Pick your date

Choose the day that fits your trip. Tours run regularly through the season.

Reserve online

Secure your spot in under a minute. No phone calls, no back-and-forth.

Show up & savor

Meet Mike in Chatham. The Cape, one bite at a time.

Pick your date below.

Good to know

Before you book.

Everything you need to know — and a few things you didn’t know to ask.

Cancellation

Free up to 24 hours before the tour.

Rain or shine

We run anyway. Bring an umbrella if needed.

Easy walking

1 mile across 3 hours. Relaxed pace, plenty of stops.

Solo travelers

More than welcome. Plenty come solo.

More questions

Do I need to book in advance?

Yes — tours fill up, especially in season. Walk-ups aren’t guaranteed.

What should I bring?

Comfortable shoes, weather-appropriate clothing, and an appetite. A small bag for souvenirs doesn’t hurt.

What kinds of food will I taste?

A real mix — fresh seafood, Filipino dishes, tavern comfort food, hand-pulled drinks, and handmade ice cream. Sweet and savory, side by side.

How much food is included?

Roughly the equivalent of a hearty lunch, served in tasting-sized portions across all stops. You’ll leave full — never stuffed.

Are drinks included?

One alcoholic beverage is included, with non-alcoholic substitutes available. Additional drinks can be purchased at most stops.

Can other dietary restrictions be accommodated?

Yes — please note any allergies or restrictions when booking and we’ll coordinate with each stop in advance. (Non-seafood options are covered above.)

Can I shop during the tour?

Yes — some stops include browsing time, and Mike will point out great shops to revisit after the tour ends.

When’s the best time to take the tour?

Tours run midday, making them a great lunch option before an afternoon of exploring Chatham. Weekdays are typically less crowded.

Are cameras allowed?

Encouraged. Tag @mike13cft if you post — Mike loves seeing it.