Chatham is located at the "Elbow" of the Cape surrounded on three sides by water, halfway between Falmouth and Provincetown. Known as "a drinking town with a fishing problem" this affluent area has been supported by the fishing industry for centuries.
6:00am (or earlier): Sunrise at Chatham Lighthouse Beach
If you are ambitious enough to arrive at #Chathamlight before sunrise your Instagram followers will greatly appreciate it. Images of Chatham Lighthouse are ubiquitous and make a great a keepsake for your time on the Cape.
Winner of 2017 Best of Boston for Brunch, Cape Cod and actually located at Chatham Airport. This unassuming breakfast spot is a Sunday morning routine for summer residents. Menu items like Red Flannel Hash and Lemon Ricotta Pancakes gives customers eclectic options compared to a typical greasy spoon.
Partnering with Chatham Bars Inn, the Atlantic White Shark Conservancy provides guests with the opportunity to shadow a team of scientists conducting research off the coast of Chatham. Great White Shark Expeditions depart Mondays and Thursdays and are $2500 with up to five passengers. As the only tours offered on the Cape that directly benefit white shark research, a large portion of the trip fee is tax deductible. Registration for the trip also includes participants’ entrance at The Chatham Shark Center. This experience wasn't available ten years ago as shark tourism has grown as the amount of sharks migrating to the warmer waters of the northeast every year increases.
Lunchtime at "CBI" (Chatham Bars Inn) is the place to be seen, evident by the expensive sports cars and luxury vehicles that litter the valet lot. Not too long ago the quality of food might have been considered an after-thought compared to the amazing views and sea breeze but not anymore. With the creation of the Farm at Chatham Bars Inn, Chef Anthony Cole has turned the many dining venues on this property into a farm to table foodie destination. Another great Cape Cod dining experience here is the Essential New England Clambake that is served Sunday through Thursday during the Summer. Advanced reservations are required.
Main Street in Chatham is as quaint of a town as you will find, hosting a famous 4th of July Parade every year. It gets so packed local residents will put out beach chairs along the parade route days in advance to reserve their spot. No vacation to Cape Cod is complete without a stop to Puritan Clothing to stock up on the latest Vineyard Vines outfits. I highly recommend Impudent Oyster right off Main Street for a quintessential Cape Cod Seafood Dinner. The ambience and lighting is subdued and conducive to great company and conversation. You must order their signature dish, Impudent “Pho” Bouillabaisse, a variety of local seafood served in a mini cast iron dutch oven.
7:30pm: Catch a few Innings of Cape League Baseball
This Yankee Magazine write up describes the scene perfectly. "Veterans Field turns magical when the lights come on and wisps of fog float in from offshore, and fans carrying lawn chairs and picnic blankets start filling the grassy spaces surrounding the playing field. All the diamonds shine in the Cape Cod Baseball League, the best collegiate wooden-bat league in the world–but none sparkles like the home of the Chatham Anglers. Part of the fun: picking out which college stars will become Major League players in just a couple years’ time. Another part: Admission is free."
If you spent summers in Chatham during your 20's, you know the Squire. If you have ever attended a wedding that had trolley transportation in Chatham, you also know the Squire. This local watering hole is very popular with college kids which causes this bar to get packed around 10pm. I recommend bellying up to the bar before that to have a chance at a seat. They have entertainment Monday, Tuesday, and Wednesday night and just like their slogan on their website says, this is "where friends get together".