Village LIFE: Charming Chatham

Cape Cod Life  /  June 2019 / , , , , ,

Writer: Christopher Setterlund / Photographer: Josh Shortsleeve 

Village LIFE: Charming Chatham


Cape Cod Life  /  June 2019 / , , , , ,

Writer: Christopher Setterlund / Photographer: Josh Shortsleeve 

Where heritage meets modern living

Lori Whalen

Perhaps no other village ties together modern chic and quintessential classic Cape Cod quite like Chatham. It still maintains its image as a hardworking fishing village while also laying claim to luxurious resorts and high-end shops on its picturesque Main Street. It is miles of pristine beaches and acres of fine golf courses. It is history and it is the future. When one asks where to go to feel all of what Cape Cod was in the “good old days” while also enjoying the luxuries the 21st century provides, there can only be one answer: Chatham.  

The town of Chatham includes smaller villages of North Chatham, South Chatham and West Chatham, bordered on the west and north by the town of Harwich, the south by Nantucket Sound, and the east by the Atlantic Ocean. It is the link to the sea that has defined Chatham and its residents for centuries. Whether it’s the fleet of fishing boats passing by Chatham Lighthouse at sunrise, or the crowds of sunbathers finding their own slice of paradise at popular beaches such as Harding’s Beach, Lighthouse Beach, Ridgevale Beach or Forest Street Beach, Chatham and the ocean are forever connected. 

Chatham’s slow evolution from a fishing village to seaside resort began at the end of the 19th century with the creation of the Cape’s first resort hotel. The concept of a resort hotel was brought to the forefront in 1889 by the Chatham Real Estate Trust, led by the future owner of Jordan Marsh, Eben Dyer Jordan, and Edward Taft, president of the New York & Boston Dispatch Express Company. The 30,000-square-foot appropriately named Hotel Chatham would open in July 1890 to much fanfare. Its first few seasons were booming with amenities like a large horse stable, bowling alley, an ice house, and bath houses, routinely filling the hotel to capacity. However, the Panic of 1893, coupled with the seclusion of the hotel that made it difficult to reach in the days before automobiles, spelled a premature end for Hotel Chatham. It sat in limbo for years before being torn down in 1910. In 1922 the grounds upon which the Cape’s first luxury resort sat would be redeveloped as the Eastward Ho Country Club, which is still in operation today.  

Chatham’s second attempt at a luxury resort would achieve much greater success. In 1914 Chatham Bars Inn would open on the beautiful Shore Road facing the Atlantic Ocean. From its roots as a semi-private hunting lodge for the wealthy elite of Boston, to the $100 million renovation by current owners Capital Properties upon purchasing the hotel in 2006, Chatham Bars Inn has seen as much change in its beloved hometown during its century in existence as it has inside its own walls.

Chatham as a whole has seen its coastline ravaged by erosion in some spots. This includes the barrier beach now known as North Beach Island—it was for decades a community of cottages accessible via oversand travel coming down from the north through Orleans. In January 1987 a Nor’easter tore through the barrier beach directly in front of Chatham Lighthouse, exposing the immediate coast to the ravages of the Atlantic Ocean. Twenty years later, in April 2007, another break occurred, this time south of the lighthouse, transforming North Beach into the island it is today.  Though the state of Chatham’s coastline might be in a constant state of flux, one can count on some things in this village to remain virtually the same.

Several longtime businesses lay a stone’s throw from the beaches along Chatham’s beautiful Main Street. For a day of prime shopping, one can step into stores like The Mayflower Shop, which first opened its doors in 1885. The Mayflower specializes in unique gifts for home and family, going beyond the typical. A few doors down is a Cape Cod original. Puritan Cape Cod opened its Chatham clothing store in 1925, and now in its third generation of management by the Penn family, it is an institution dedicated to earning its relationship with its customers. For the avid reader, Yellow Umbrella Books, also on Main Street, has been a purveyor of fine literature since 1980. Whether looking to create a fresh meal at home, or pick out a special Cape Cod gift for a friend, the Cape Abilities Farm Market on Main Street near Chatham Lighthouse is a great place to stop. It has tomatoes, greens, fruit, pies from Centerville Pie Company, hanging plants, clothing from local artisans like Cape Cloth, and is staffed by Cape Abilities participants.

When you’re done shopping, there is plenty of food and drink to be had. One does not have to even leave Main Street to grab a bite at the TripAdvisor top-rated Chatham Wine Bar. Conveniently located in the same building as the romantic 4-star Chatham Inn, this restaurant offers a thorough wine menu and seasonal outdoor dining on its terrace. For those desiring a pub atmosphere, the iconic Chatham Squire is only a few doors down on Main Street. Since opening in 1968, it has been known equally for its menu and entertainment. It’s the perfect place for a family meal, or a fun spot to dance the night away. A short trip west along Route 28 will bring the legendary Pate’s into view. This landmark restaurant, specializing in prime cuts of beef, seafood, and cozy décor, has been pleasing patrons since 1957.

Chatham is more than food and drink, though—the town boasts a thriving art scene. The nonprofit Cape Cod Creative Arts Center on Crowell Road has been nourishing the artistic sides of both young and old since 1969. Their piece de resistance is the annual Festival of the Arts, held at Chase Park on Cross Street during the third weekend of August. It features the work of more than 120 artists both local and national.    

Chatham Light
Jeff Dannay

A wondrous day of checking out Chatham’s Main Street would not be complete without splicing in a little history with one’s entertainment. The Chatham Orpheum Theater originally opened at 637 Main Street in 1916 during the silent era of film. The Orpheum captivated audiences with first-run movies until its first chapter ended in 1987. It closed and became a CVS. In November 2011, after CVS had left the building, a grass roots team raised the $1.2 million to buy the building, and then the $4 million to renovate the old theater into a modern cinema. The return of the beloved movie house has earned praise from locals and visitors, even legendary director Steven Spielberg. 

One would be truly missing out on the heart and soul of Chatham if they did not spend some time out in nature exploring. A perfect place to get lost among the untouched scenery of Cape Cod is at the Monomoy Wildlife Refuge on Wikis Way. Established in 1944 as a protective habitat for migratory birds, the refuge is 7,604 acres in total, although due to the shifting sands only 40 acres remain connected to the mainland, with the rest of North and South Monomoy Island lying just offshore. For those wishing to see the islands more closely, there are island excursions offered by companies such as Monomoy Island Ferry, based out of Stage Harbor, which has been in business since 1989.

There are also a number of other delightful options to enjoy the outdoors in Chatham. One can stop, sit, listen and enjoy the sights of the fishing fleets departing or returning with their catches at Stage Harbor or at the Chatham Fish Pier on the Barcliff Avenue Extension, where one can also enjoy a drink and a bite to eat at the Chatham Pier Fish Market. It was featured by CBS Boston as one of the best lobster shacks on Cape Cod in 2014, after all! One can also enjoy a pleasant day outdoors sitting on the sand at Oyster Pond, or cycling along the Old Colony Rail Trail, which begins at the intersection of Depot Road and Hitching Post Road. It is possible to ride the trail all the way north to Wellfleet, or west through Yarmouth.

Chatham Break in Monomoy Island
Josh Shortsleeve

Of course in order to truly appreciate all that Chatham has in the present one should take a look at some of the places where it all began. The Chatham Historical Society itself resides in the Atwood House & Museum on Stage Harbor Road—a restored 1752 home with exhibits and galleries inside celebrating Chatham’s past. Get up close and personal with history less than a mile from the Atwood House by visiting the Godfrey Windmill on Shattuck Place. Built by Col. Benjamin Godfrey in 1797, it is one of the oldest surviving wooden windmills on Cape Cod and was completely restored in 2012.

An intricate tapestry of modern chic and quintessential classic, Chatham is firmly standing in the 21st century while still holding on to its fishing village roots. Visitors may stay close to Main Street and be completely satisfied with their trip to the “elbow” of Cape Cod. They may also venture far off the beaten path to areas where cell phone reception is spotty at best and become lost in nature. Sunrises at Lighthouse Beach, seal cruises to Monomoy, a glass of wine at the Chatham Wine Bar, burgers at Mom & Pops Burgers, cycling the Old Colony Rail Trail, or swimming at Harding’s Beach, there is no shortage of ways that this village can enchant those who visit. Those who call it home already know of the magic of Chatham’s village life.

Atwood House & Museum

Celebrating 96 years of local history, culture and art, the Museum, near downtown Chatham, features 11 galleries and a gift store. New exhibits this year include “Main Street Cape Cod,” the historic NC-4 first transatlantic flight, and an archaeological dig. Enjoy interactive exhibits with fun for all ages.

347 Stage Harbor Road. 508-945-2493. chathamhistoricalsociety.org


With an ever-changing cache of one-of-a-kind consigned finds, Bungalow is the go-to shop in town for stylish home furnishings and décor. Stop by the store to experience a truly at-home feel. Bungalow’s design team also offers staging and consultation services to breathe new life into your home.

1291 Main Street. 774-316-4506. bungalowcapecod.store

Chatham Sign Shop

Stylish handcrafted quarterboards and house number signs in a variety of motifs feature durable marine enamels and 23-karat golf leaf. These unique home accents are truly delightful. Call for a free brochure. Chatham Sign Shop ships worldwide. These are wonderful gifts for all occasions.

40 Kent Place. 800-547-4467. chathamsignshop.com

East Wind Silver Co.

East Wind Silver Co., the Cape’s premier choice for sterling silver jewelry since 1999, closed its brick & mortar shop and now brings you the same beautiful jewelry online at www.eastwindsilver.com. East Wind makes the Chatham Hook ™ and Chatham Fish Cuff bracelets; Cape Wave ™ jewelry; and the new seabangles ™ collection. It also stocks genuine Cape Cod Jewelry ™ at unbeatable prices. The online shop in Chatham ships most orders within 24 hours.


Fisherman’s Daughter

Taylor Brown, a local fisherman’s daughter and shellfisherwoman, has turned her passion for protecting the ocean into a thriving eco boutique business. Her Fisherman’s Daughter Collection features the softest handmade, eco-friendly clothing and accessories with charming nautical designs. The boutique also carries a curated mix of over 50 eclectic and ocean-inspired artisans and designers.

521 Main Street. 508-292-5463. @fishermansdaughter fishermansdaughtermarket.com

Mom & Pops Burgers

Open year-round, Mom & Pops Burgers has been voted Best Burger by Cape Cod LIFE readers in 2018 and 2019. Mom & Pops mission is to serve food they grew up on and love, sourcing only the highest quality, freshest ingredients. Beef butchered and ground in-house daily. Hand-cut fries. Every order cooked to order.

1603 Main Street. 774-840-4144. momandpopschatham.com

Wheelhouse Bike Co.

Wheelhouse Bike Co. is a full-service, Trek-authorized bike shop, located by the bike path entrance in Chatham. Wheelhouse has every kind of bike you need for your Cape Cod adventure, with the friendly service and local knowledge to help you explore more!

48 Crowell Road. 774-840-4156. Book your bike rental online at www.wheelhousebike.com.

Where the Sidewalk Ends Bookstore & Children’s Annex

Meet your favorite authors over a gourmet lunch! Where the Sidewalk Ends Bookstore hosts bestselling authors at the five-star Wequassett Resort. Visit the post-and-beam bookstore and children’s annex for books, educational toys and unique gifts. A breezy, covered deck, parking, and seating make this bookstore a favorite for all ages!

432 Main Street. 508-945-0499. booksonthecape.com

Christopher Setterlund

A resident of South Yarmouth, and a 12th-generation Cape Codder, Christopher Setterlund is a man of many talents. He’s a certified personal trainer, a freelance writer, and a published author. His recent titles include “In My Footsteps: Martha’s Vineyard,” “In My Footsteps: Nantucket,” and "Historic Restaurants of Cape Cod."