The best walking guide to downtown Chatham

Chatham is well known for its breathtaking ocean views, luxury shops, and outstanding seafood, but did you know that the town has a rich history as well?  When you think of Chatham, you likely envision opportunities to get out on the water or visit the many beautiful beaches, but there is plenty to see and experience just by strolling along on one of the many walking and hiking trails. Simply walk around and enjoy the natural beauty of the region. Even our repeat guests that have been coming for over 20 years are not familiar with the fun walks around downtown Chatham. We wanted to provide you with the best walking guide to all the historic sites you might have missed in the past.

Explore the history, architecture, and people in downtown Chatham by walking the many beautiful streets and beaten paths that our town has to offer. Learn how Chatham developed from a small farming community into today’s vibrant seaside village. Have you noticed the 13 informational signs scattered around town, located at 11 historic sites in town? If not, put it on your bucket list next time you are in town. From 1 to 3 miles you can take many short or long walks from the Inn. All of the historic plaques are listed below.

To start your walk, take a left out of the Inn and continue straight passing the Chatham Rotary on Stage Harbor Road, and soon you will see the Oyster Pond’s beautiful water views. Continue straight and discover your first plaque.

The Atwood School

This plaque is located at the corner of Stage Harbor Road and Cedar Street, in front of the building that is currently Chatham’s Scout Hall and it tells the story of the Atwood School. Did you know that the first owner of the Inn Doctor Keen taught students here back in the days? If you would like to learn more about Dr. Keen and the Inn’s history visit our digital guest book.

Continue straight on-Stage Harbor Road and about half a mile down you will find the second historic plaque.

The Old Atwood House

This plaque is located at the Atwood House & Museum and tells the story of the old Atwood House. Tour the dwelling built circa 1752 by a Chatham sea captain Joseph Atwood. This historical house museum offers the rare opportunity to experience Cape Cod life, art, and culture of the 18th and 19th centuries.

Continue further down Stage Harbor Road passing Bridge Street to reach the next plaque on your left overlooking the beautiful harbor.

Champlain’s Visit – Monument & Plaque

The Samuel de Champlain 1606 Voyage Commemoration Monument on Stage Harbor Road was the creation of Carol Wight, a professor at the University of Johns Hopkins, and the husband of Alice Wight, whose murals hang in the Mural Barn at the Atwood House Museum. The plaque reveals the journey of the French explorer, Samuel de Champlain. In 1605 and again in 1606 he sailed from Nova Scotia to Cape Cod exploring and mapping much of the coast along the way while searching for a site for a permanent French settlement.

Go back to Bridge Street and go over the newly renovated draw bridge overlooking Stage Harbor. Continue to the end of the street and make a left at the Chatham Lighthouse, and the beautiful ocean views will appear right in front of you.  In this location, you will find your next three plaques.

History of Chatham Light

This plaque is located on Main Street at the Chatham Lighthouse and tells the story of the history of Chatham Light. Daily tours are offered by the coast guard in season, every Wednesday from 1 p.m. – 3 p.m. This is an active lighthouse and a Coast Guard station.

Chatham Lighthouse with american flag

The Pendleton Rescue

The story of the Coast Guard Pendleton rescue is told on a plaque located at the Lighthouse Beach Parking overlook, across the Chatham Light. Since the time the plaque was installed, the story has been re-told in the book and movie The Finest Hours, available to watch at the Inn.

The Mayflower Story

This plaque is also located on Main Street at the parking area of the Lighthouse Beach overlook and tells the story of the Mayflower’s encounter with the treacherous Chatham waters. Look at the Chatham breach and the large sand bars, perhaps you will spot some seals. This is the best place in town to take photos, so do not forget your camera!

Chatham Lighthouse beach

Continue your journey down Main Street to explore Chatham’s downtown, the old village, shops, and grab lunch at the many exquisite seafood restaurants. While walking back notice all the beautiful landscapes, flowers, and trees. We can provide you with a self-guided tour of Notable Trees in downtown Chatham. Also, if you are interested in more history walks head down School Street off Main Street. This is where you will find many historic homes dating from c.1730 to the 20th century. This is the Old Village District with more than 300 properties listed on the National Register of Historic Places. Where each of the homes features a plaque.  

Once back on Main Street in downtown look for the Town Offices at the corner of Main Street and Cross Street, this is where you will find your next two plaques.

The Story of Chatham History

The plaques tell the story of Chatham’s history. The first European to land on the shores of Chatham was Samuel de Champlain, who took refuge in Stage Harbor in October 1606. The first settlers that came to what was known as Monomoit (now Chatham) were the Nickerson family in 1664.

Make a little detour and go down Cross Street to Chase Park. Make sure you take a look at the modern homes and beautiful landscaping along the way. Once you reach the park, walk all the way to the end to Shattuck Place at the back of the park to find your next plaque.

The Godfrey Windmill History

This plaque tells the story of the Godfrey Windmill. This wind-powered grist mill was built in 1797 by Colonel Benjamin Godfrey on a hill by his home on Stage Harbor Road overlooking the Mill Pond, where it served the growing needs of Chatham residents for cornmeal, a staple among early settlers.  

Chatham Windmill, Chase Park, Chatham, Massachusetts, USA

Return to Main Street and head back to the Inn for a well-deserved cup of hot coffee and some cookies. Relax on our beautiful sunny deck and get ready to explore the town further. Go back to Old Harbor Road and this time make a right out of the Inn. Just a block down you will see Depot Road, make a left and you will arrive at your next plaque and historic site.

The Chatham Railroad Depot

This plaque is located at the Railroad Museum on Depot Road and tells the story of Chatham Railroad Depot. A 2-6-0 coal-fired steam locomotive coupled to a string of freight cars waits for departure at the Chatham Railroad Depot in 1932. The Chatham Railroad Company constructed seven miles of tracks as a branch line with stations in Chatham, South Chatham, and Harwich.

Go back to Old Harbor Road and make a left heading away from town. When you reach Bacliff Ave. make a right. Go all the way to the end of the road and cross the street where you will find your next plaque.

Chatham Commercial Fishing

The plaque is located on Shore Road at the top of the stairs to the Fish Pier and tells the story of Chatham’s Commercial Fishing heritage. This is a great place to grab a bite to eat at the Chatham Fish Pier Market. Also, spend some time on the newly built Fish Pier Observation Deck, watch the boats come in, and the seals playing in the water.

Chatham Fish Pier

Whether you are a Chatham regular or a first-time visitor you ‘will find this activity worthwhile. Chatham is a town steeped in history, home to wonderful museums, historic structures, a coastline full of history as well as beautiful beaches and scenic spots, hidden architectural gems, and natural history.  What a fun way to spend your day in Chatham exploring history and enjoying the beautiful outdoors. Do a scavenger hunt and make it a goal to find all  13 plaques. Take pictures with all of them and post on our Facebook page to get a FREE Old Harbor Inn Mug. As always, our professional concierge staff with over 25 years of experience is always available to plan your vacation, give you tips on places to eat, shop, and explore. Book your stay today and let us plan your dream vacation to Cape Cod!

Colorful exterior of a shop in Chatham, Cape Cod, Massachusetts.

Visit Chatham Smart Tour on your phone and listen to the recordings on each of the sites! 

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