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Posted by Julie Loffredi, guest blogger of

A friend of mine named her daughter after the beauty of this seaside town. But Chatham is much more than a pretty name. It’s a classic New England destination that draws visitors from all over the world.
The town’s 24 square miles is often the star backdrop for vacation photo albums. Who could resist a ‘say cheese’ moment at Chatham Lighthouse Beach or Cockle Cove?
As summer fades, Chatham still maintains its photogenic charm and brings a new color wheel to adore. The locals tell me the ocean water is at its deepest navy blue, while the leaves turn a bold mixture of orange, yellow and gold.
Chatham beach during fall

Photo: Chatham during fall

The fall season brings much more than attractive scenery, though. Un-crowded streets, traffic-free bridges, and discounted room rates make this an ideal autumn destination. (And, of course, those Chatham lobster rolls taste good all year long.)
What to do:
October is jam-packed with fall activities the entire family can enjoy — so be sure to pack that ‘ole Black Dog sweatshirt you scored from your last trip to the Vineyard – you’ll likely need it while strolling the streets of Chatham on cool nights. Here are my top picks:
Oktoberfest in Chatham. Beer garden tent with bratwurst and good music. Lines start forming at noon, so get there early! (Oct 25)
Chatham Oktoberfest

Photo: Oktoberfest in Chatham

Pumpkin Patch. Pick out a pumpkin at the First Congregational Church on 650 Main Street. Proceeds benefit the Chatham Children’s Fun.  (Oct 1-31)
Autumn Art Sale.  View the latest artwork for sale by Cape Cod artists at Creative Arts Center on 154 Crowell Road in Chatham. (Oct 10-11, 13)
Pumpkin People in the Park.  Take a stroll through Kate Gould Park and the Chatham Bandstand while enjoying the autumn-inspired displays.  (Oct 17-31)
Where to stay:
My favorite hotel is Wequassett Resort & Golf Club, located on stunning Pleasant Bay. I stayed here with my husband and daughter a few years ago and felt like a Kennedy!

Photo: Wequassett Resort & Golf Club in Chatham

This hotel scores high marks for customer service. We stayed in mid-September and seemed to have the entire resort to ourselves. I love little touches of detail – like the housekeeper would leave behind a children’s book and some treats for my daughter. My kid also got a kick out of a complimentary golf cart ride to our room (suites are scattered around the property) and free pool toys to play with.
Another perk: guests at Wequassett Resort can tee up at the neighboring Cape Cod National Golf Course.
Julie’s Tip: The room rates go down dramatically in October before it closes for the season. Go for a water view.
Chatham Bars Inn is another popular pick for those who like a bit of hotel glamor. The resort sometimes offers Groupon deals and discounts during off-season. is great resource for those looking for accommodations in Chatham. (Check this link for a full list) And for more information on visiting Chatham, check out this link.
Julie Loffredi (@julieloffredi) is an award-winning broadcast journalist who regularly hits the morning show circuit to dish about the latest travel trends. Julie has appeared on NBC TODAY, Good Morning America, CNN, Hallmark Channel and Fox News Channel. You can read more of her work at