Ultimate Guide to Chatham Main Street

Chatham boasts one of the most popular village centers on Cape Cod, and with good reason. Chatham Main Street is loaded with things to do: restaurants, cafes and pubs to enjoy, along with shops, and boutiques and galleries to browse. If you want some insider tips about what to do in Chatham center when you stay at nearby Handkerchief Shoals Inn, this local guide is for you.

Chatham Restaurants

If you've already dined west of Handkerchief Shoals Inn in Harwich Port center, it's time to try some of the popular draws in Chatham.

Sweet Tomatoes

Address: 790 Main St
Hours: 11AM - 8PM
Type of Food: Pizza

Pizza is a staple in the average person's diet for a reason! Come to Sweet Tomatoes for a light and tasty thin-crust pizza or try a calzone or a goat cheese salad (our staff favorite!) This is a family-friendly, fast-casual restaurant with a laid-back vibe and very casual outdoor seating, great for a summer evening as you wind down from a long day at the beach. Super friendly staff from all over the world!

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Impudent Oyster

Address: 15 Chatham Bars Ave, Chatham
Hours: See website for up-to-date seasonal hours and serving times
Type of Food: Seafood

While other restaurants serve seafood, the Impudent Oyster, just off Main Street, is famous for some of the best seafood in town. An elegant restaurant and bar, just steps from all the shops.

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Captain's Table

Address: 576 Main St, Chatham
Hours: Tuesday - Sunday: 8:30AM - 3PM
Type of Food: Seafood etc.

This cozy breakfast/lunch diner serves an eclectic mix of seafood or wraps, homemade soups, breakfast items and salads for an affordable price. With indoor or outdoor seating options, you can enjoy fish & chips with a beer in front of a full screen TV, or watch Main Street go by from a cozy bistro table on a charming patio. Casual and family friendly with a children's menu for 12 and under.

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Bluefin Sushi

Address: 513 Main St, Chatham
Hours: Tuesday - Sunday: 5PM - 8PM
Type of Food: Japanese

Sushi isn't for everyone, but it has dedicated fans. This is the only sushi restaurant for miles, and it does not disappoint. Enjoy the artistry and taste offered by the chefs at Bluefin, or enjoy a drink with other Asian-inspired menu items.

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The Chatham Squire

Address: 487 Main St, Chatham
Hours: 7 days a week, 11:30 AM-1:00AM
Type of Food: Seafood, Bar & Grill

A local institution, the Chatham Squire bar and restaurant is also well known all over Cape Cod. You are sure to find something you like on the menu, but how to choose between the steamed local seafood, raw bar combo, lobster dinner, Squire carbonara, and a filet mignon? Be sure to bring your appetite and let it decide. Don't forget to sample some great local Cape Cod brews while you are at it, starting with the Squire Lager! A hopping and popular place with events and entertainment all year round. You haven't been to Chatham if you haven't been to The Squire!

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Chatham Shopping

Needing a kitchen gadget? Wanting to splurge on an authentic and local souvenir or a Cape Cod bracelet? It's time to check out the local shops, for everything from clothing to candy.

The Squire Shop

Address: 490 Main St, Chatham
Hours: 10AM - 6PM
What they Sell: Clothing and gifts

Looking for Cape Cod bling? The Squire Shop could have something in store for your wardrobe! Find everything from hoodies to tumblers here. Be sure to pick up a souvenir of your visit to Chatham with a T-shirt or cap from the bar that's a Cape Cod favorite!

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Chatham Candy Manor

Address: 484 Main St, Chatham
Hours: 10AM - 5:30PM
What they Sell: Chocolates

A third-generation family-owned, year-round business. This traditional candy store will dazzle you with delectable chocolates and specialty items such as chocolate scallops and smores bars. More than 67 years of craft have gone into these mouthwatering choices, made the old-fashioned way in copper kettles. Don't forget to save some for your significant other!

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Ducks in the Window

Address: 507 Main St, Chatham
Hours: 10AM - 5PM (Monday, Thursday - Sunday)
Closed Tuesday and Wednesday
What they Sell: Souvenirs and gift items

This quirky shop sells rubber duckies of all shapes and sizes. Buy one that's dressed in your favorite color, or surprise your children with a duck dressed as a unicorn! It's a fun variety store with a charming window display that can appeal to anyone.

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Chatham Fine Art

Address: 492 Main St, Chatham
Hours: 10:00 AM -6:00 PM 7 days/week as of May

With its dramatic coastal scenery, Cape Cod has long attracted artists to its ocean beaches, moody marshes and pitch pine forests. Here in Chatham, as in Wellfleet and Ptown, small galleries dot the town center, where you may check out the work of local artists as you window shop and wander the town.

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Artful Hand Gallery

Address: 459 Main St B, Chatham
Hours: 10:30AM - 5:30PM

A fun store with jewelry pieces to buy, art to admire, and other items for your viewing pleasure. As much a souvenir shop as a gallery, Artful Hand offers artistic pieces from every craft.

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Yankee Ingenuity

Address: 525 Main St, Chatham
Hours: Call at 508-945-1288 for more information
What they Sell: Gifts, Cape Cod souvenirs, jewelry, fine art photography

Buy unique craft items inspired by local sights and created by local artists. The photography on display here is some of the most eye-catching for those who love the views of the beach, ocean, and Cape lighthouses. With shelves full of eclectic finds, Yankee Ingenuity is not your average gift shop!

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