A Guide to Chatham’s Main Street and Beyond

Chatham is one of (if not the most) walkable towns on Cape Cod. It’s also one of the most endearing, combining a classic “Main Street” atmosphere with modern amenities and a wide variety of destinations.

Since the center of Main Street is only a 15-minute walk from Chatham Bars Inn, we wanted to break down all of our favorite walkable must-sees for our guests. When you’re ready to take a break from the beach, make one of these venues your destination!

Cultural Destinations

Despite having a population of just over 6,000, Chatham is full of cultural destinations guaranteed to wow any visitor. From film to theater to fine art, you’re sure to be entertained and inspired.

Image courtesy of The Orpheum Theater


637 Main St., Chatham, MA 02633

(508) 945-4900


The Orpheum Theater opened back in 1916 and, for 72 years, gave locals and tourists alike a place to gather and enjoy the silver screen. When the movie theater shut its doors in 1987, it left a cultural void in Chatham and Cape Cod at large.

Fortunately, in an effort spearheaded by founding president Naomi M. Turner and a team of local volunteers, the Orpheum was completely restored and re-opened in early 2013. The theater retained its classic vintage feel but gained the state-of-the art technology necessary to show first-run movies as well as classics such as Jaws and Raiders of the Lost Ark.

Image courtesy of The Monomoy Theater

Monomoy Theater

776 Main St., Chatham, MA 02633

(508) 945-1589


Fans of the theater should make a point of taking in a show at the charming Monomoy Theater during their time in Chatham. The summer season is jam-packed with first rate entertainment from the classic to contemporary to musicals, with a different show each week from June through August.

Image courtesy of Gallery Antonia

Gallery Antonia

1291 Main St, Chatham, MA 02633

(508) 469-4020


Chatham’s local art scene is rich and varied, heavily inspired by the gorgeous landscapes of Cape Cod. If you’re looking for a gorgeous piece of art to take home to remember your trip to Chatham, or if you just want to surround yourself with beauty, make sure you check out Gallery Antonia on Main Street.

Food & Drink

Chatham Bars Inn features a variety of world-class dining experiences, including fine dining at STARS, upscale pub food at the Sacred Cod, coastally-inspired seafood at the Beach House and a host of private dining options. If you’d like to stroll into town for a meal or a cocktail, however, you’ve got plenty of options.

Image courtesy of The Impudent Oyster

Impudent Oyster

15 Chatham Bars Ave., Chatham, MA, 02645

(508) 945-3545


If you’re ready to eat, get to the Impudent Oyster. Their focus is on local seafood, and plenty of it. The generous portions are sure to satisfied the hungriest diner, but don’t be fooled by the large plates: this is upscale dining at its best. Despite prevalent rumors to the contrary, the building was never a church. Formerly a local fisherman's hangout called The Sign of the Surf, it was renovated under new ownership using reclaimed pews and stained glass from a church in Maine.

Image courtesy of The Chatham Squire

Chatham Squire

487 Main St., Chatham, MA, 02633

(508) 945-0945


We’ll be the first to admit that Chatham isn’t known for its rowdy nightlife. If you’re looking for an evening out on the town, however, you’ll probably find yourself enjoying last call as The Chatham Squire. The Squire features live music, food and drink, as well as the latest closing time in town (1 AM).


Chatham's Main Street is a great place to shop, and not just for souvenirs - the town is home to everything from high-fashion boutiques to casual clothing stores.

Image courtesy of Sara Campbell

Sara Campbell

578 Main St., Chatham, MA, 02633

(508) 348-1702


The Boston-based fashion label Sara Campbell features gorgeous clothing for women of all ages. If you're in town, make sure to pick something up - Sara Campbell is so dedicated to exceptional, personal customer service that they don't have an online store.

Image courtesy of The Black Dog

Black Dog

628 Main St., Chatham, MA, 02633

(508) 945-3026


If you're looking for casual apparel with a Cape Cod feel, check out the Black Dog on Main Street. They've got apparel for the whole family, including your pooch.


Cape Cod is one of the most beautiful places in the world and Chatham Bars Inn is situated right in the middle of some of the region’s finest natural splendor. Do yourself a favor and make time to take it all in.

Image courtesy of The Monomoy National Wildlife Refuge

Monomoy National Wildlife Refuge

30 Wikis Way Chatham, MA 02633

(508) 945-0594


At 7,604 acres, the Monomoy National Wildlife Refuge is an enormous and gorgeous stretch of nature that includes everything from ocean habitats and dunes to freshwater marshes and ponds. Founded in 1944 to provide a habitat for migratory birds, it’s also a vital part of the Cape Cod ecosystem.

The route to the Wildlife Refuge is more or less a straight line on foot or by bike. Head south down Shore Road, which eventually turns into Morris Island Road. You’ll pass the Chatham Light and eventually go over a narrow causeway to Morris Island. Don’t be deterred by the private road signs at the end of the causeway - you’ll eventually come across the refuge’s driveway to your left. It should take you about 45 minutes on foot or 15 minutes on bike to get there.

Image courtesy of Chatham Bars Inn

Chatham Lighthouse

37 Main St., Chatham, MA 02633

Chatham Lighthouse is one of Chatham’s most enduring symbols. Two towers were actually constructed at this site in 1808, though one was moved in 1923 and became Nauset Light near Eastham.

The lighthouse is actually visible on the way to the Monomoy National Wildlife Refuge. Just head south down Shore Road, which will turn into Morris Island Road, and you should pass it in no time.

On the Water

If you’re on Cape Cod and you don’t get out on the water, you’re depriving yourself of some of the most enjoyable and memorable experience that the region has to offer. While there are some charter boat companies out there (like Down Cape Charters), if you’re a guest at Chatham Bars Inn, your best bet is calling up the concierge desk and reserving something directly through us. The following experiences are just a taste of what we can offer.


Experience the daily routine of a lobsterman as you participate in the excitement of hauling, emptying and baiting the traps on Lob Star.

Learn more about our boating program and call 800.527.4884 to reserve your spot.


Hop on StarStruck and head offshore in pursuit of blue water species such as Bluefin tuna. StarStruck is fully equipped with top-of-the-line electronics and the finest fishing tackle.

Learn more about our boating program and call 800.527.4884 to reserve your spot.

Shark Expeditions

Ride with the Atlantic White Shark Conservancy as they pull beacons, tag sharks and conduct their vital research. You might even get your picture with a great white!

Learn more about our shark expeditions and reserve your spot by calling 800.527.4884.

Whale Watching Tours

Imagine being up close and personal with a 50-foot, 66,000 pounds humpback whale as it works with its pod to hunt mackerel and herring in deep blue waters of the Atlantic. That’s likely what you’ll see when you book your whale watching tour with Chatham Bars Inn.

Learn more about our whale watching tours and reserve your spot by calling 800.527.4884.

Seal Cruise

Aunt Lydia's Cove is home to hundreds of gray & harbor seals. This tour is an opportunity to see them up close and learn about their eating and migratory habits.

Learn more about our boating program and call 800.527.4884 to reserve your spot.


Sail the open Atlantic with us! These sailing adventures are family-friendly - we even offer sailing lessons for kids!

Learn more about our boating program and call 800.527.4884 to reserve your spot.


Chatham is an all-around family-friendly destinations, but if you’ve got an afternoon to kill with the kids, these are your must-see spots.

Image courtesy of Ducks in the Window

Ducks in the Window

507 Main St, Chatham, MA 02633

(508) 945-0334


Ducks in the Window is one of those places that you have to see to believe. Featuring the world’s largest selection of rubber ducks, it’s an incredible place to take the kids and pick out a fun, unique souvenir for friends and family back home. Ducks in the Window also offers extensive personalization options, meaning that your duck will be one-of-a-kind.

Image courtesy of The Chatham Shark Center

Chatham Shark Center

235 Orleans Rd, North Chatham, MA 02650

(508) 348-5901


Great white sharks have captured our imaginations for decades (or at least since “Jaws” came out), but they remain deeply misunderstood creatures. The Chatham Shark Center is full of captivating and interactive exhibits that will entertain and educate both you and your kids as you learn about sharks and the important role they play in our environment.

Header image courtesy of Irishman19 under a Creative Commons 4.0 License.

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