Charm in Chatham | The Perfect Cape Cod Day Trip

Take a tour of the scenic and charming town of Chatham in Cape Cod

I always have a little fun when I am describing the geography of Cape Cod to people who are unfamiliar with the area.  Flexing a bicep, I can use my arm to point out every part of the Cape from Upper to Mid, from Lower to Outer.  And there is no better way to describe the charming community of Chatham, than as the elbow, the great connector where the Nantucket Sound and Atlantic Ocean converge and the historic Cape Cod National Seashore begins.

Enjoy a perfect day trip to Chatham in Cape Cod

Founded in 1656 after an intense trade involving axes, hoes, knives, some schillings, a hat and coats, Englishman William Nickerson bought the land, originally known as Monomoit from the Monomoyick,  a member of the Wampanoag Tribe. The area was renamed after Chatham, England, and was incorporated in 1712. For over 200 years, the area flourished with the success of several industries including fishing, shipping and whaling.  When train travel finally hit the shores in the late 1880s, the town became a popular summer destination as families could finally travel easily from as far as New York, Boston and other mainland points. While the summer season still brings in almost double the population,  the 21st century has seen the area grow as an all season town as well.

Here are just a few highlights of things to look for when you’re planning a day trip:

Enjoy a perfect day trip to Chatham in Cape Cod


What makes Chatham so unique is that it has managed to keep it’s small and historical charm while balancing a sophisticated and vibrant social life.  Walking down Main Street, you feel transported in time, but also very current and fashion forward with the unique assortment of restaurants, shops, art galleries, antique stores and design studios. And of course, no walk through any town or street in Cape Cod would be complete without the gorgeous hydrangeas and flowers that brighten every block and side street as you stroll along.

Enjoy a perfect day trip to Chatham in Cape Cod

For a quick bite, the Chatham Squire is always a solid good time and meal, that is if you have at least an hour to wait during the high season. It’s your general assortment of grill and seafood and has a lively bar and atmosphere of both locals and tourists. The other nice spot is The Wild Goose Tavern, known around Chatham as ‘The Goose. It’s located on-site at The Wayside Inn, and offers downtown Chatham’s only outdoor dining. The Goose serves an inventive menu of locally sourced seafood and other ingredients, including organic and gluten-free dishes, to suit most appetites or diets. 

Enjoy a perfect day trip to Chatham in Cape Cod

The architecture and curb appeal of the homes that are located just steps around town are also a delight to walk by.  The winding lanes include dozens of cottages and expanded capes covered in flowers and classic white picket fences and trellises. American flags fly on most doorsteps and there is always some festive lighting no matter what time of year.

Enjoy a perfect day trip to Chatham in Cape Cod


Just down the road is Lighthouse Beach and the famed Chatham Lighthouse.  If you’re just here for the day, wait for a timed meter spot and take a walk and scenic view stroll down to watch the seals and surf. The lighthouse, the second oldest on Cape Cod, was built in 1808, and is one of the few lights still in operation 24 hours a day.

Enjoy a perfect day trip to Chatham in Cape Cod


The Chatham fishing pier has been one of my favorite spots to visit since my kids were little – and a must on any parents to do list wherever you are staying on the Cape.  The free observation deck is open to the public and you can watch as the fishing boats come in and offload their catch of the day. But that’s not the fun part. The fun starts with the dozens of seals that gather around the boats, right under the docks and hulls to snack on the leftovers and spillage as the fish are unloaded from the boats onto the conveyor belts. It’s the best free zoo in town!

Enjoy a perfect day trip to Chatham in Cape Cod


Very few properties evoke the elegance and coastal chic charm that the Chatham Bars Inn, the queen of all the resorts on the Cape, does. From the moment you pull  around the floral lined circular drive away, and climb up the grand steps that overlook a magnificent ocean view, you know this is a very special place. The grand lobby will have you thinking twice that you are 45 miles out on an island peninsula – it’s grandeur would rival any major city hotel.  This is a must to stop by when you’re in town, even if it’s just for a drink on their veranda, or down on the beach side cabana bar (the mudslide is heavenly).

Enjoy a perfect day trip to Chatham in Cape Cod

The property is also a Hydrangea lovers dream (yes, I’ve been known to drive by just to see the blooms). From the front lawn and back entrance, to the private rental cottages that are part of the expansive property, every inch of the resort is covered in them.  And just a short walk down the road is the famed Hydrangea Walk House. If you are lucky enough to be a guest, you will find nothing less than 4-star treatment and services throughout the entire resort.

Enjoy a perfect day trip to Chatham in Cape Cod


If you’re looking for a more structured itinerary, this would be my suggestion:

9am – Chatham Fishing Pier 
10am – 3pm Stroll, Shop and Eat on Main Street
3pm – 4:30pm Head over to Chatham Light to site see
5pm – Happy Hour at Chatham Bars Inn

Stay for dinner at the Inn, head back in town to the Wild Goose, or end the day with dinner at my favorite restaurant back towards Mid Cape in Orleans, The Land Ho!

view full gallery

click on photos to zoom

map this
pin this
Previous articleIsland Hopping | Getting to Martha’s Vineyard, Nantucket and Block Island
Next articleThe Cliff Walk of Newport, RI | Sunday Morning Stroll