Hip Daddy

06 23

COVID THROWBACK- Hip Daddy Travel: Chatham Is The Place To Be.

Originally published 6/19/19

Cape Cod is the quintessential summer vacation spot.  From Provincetown to Osterville to Falmouth, the Cape is full of amazing quaint towns you should explore.  However, given Hip Daddy is straight and to the point, you need to look no further than a town called Chatham– the SPOT you need to visit if thinking about a Cape summer vacation.  (And stop Googling right about now…yes it is known to be the “Summer Home to The Great White”..but that’s just poor marketing strategy and not what Chatham is all about.  It rocks, plain and simple…)

That said, below is your Hip Daddy Travel Guide for Chatham, Cape Cod, Massachusetts.


1.) Chatham Bars Inn.  This is the ultimate in Cape luxury.  Situated on the water and close to town, CBI is an amazing resort that will “have you at hello” and will leave you happy as a clam…that’s pretty enticing.  The Main house is eye candy, complete with beautiful accommodations as well as a patio and sitting area where you can enjoy a glass of wine while watching the fishing boats come in to the Chatham Fish Pier.   The Spa is amazing, you might think you are at Canyon Ranch.  And they have an awesome pool where the kids can play all day while Hip Daddy soaks in the Cape sun.   And yes, the kid’s program is award-winning.  Overall, it is worth the hefty price tag.

2.) Wequasset Inn.  This a Hip Daddy favorite.  Unlike CBI, it is on the outskirts of town and situated on Pleasant Bay…but still only a short drive to town.  It is a smaller, more private Inn with amazing service and a beautiful property.  The Outer Bar is a great place to wind down after a long day, and the food is delicious…calamari!  The pool is large and awesome,  and the nearby fire pit even makes the often cooler Cape nights enjoyable.  And even better, the children’s program is top notch, complete with a Pirate ship playground.   Simply impeccable all around.  Did we mention the fire pit?…

3.) Wayside Inn.  A bit more affordable, without the bells and whistles, but just right.  It is located right on Main Street so you are in the action at all times.  And yes, they even have a small pool which is a great treat to have after a long day at the beach.


Breakfast: Hangar B Eatery.  This place is located at the small Chatham airport.  The food is great, and you get to watch a bunch of ‘weekend warrior’ pilots land their small aircraft on the short runway while eating a delicious omelette…exciting to say the least!   Yes, the kids will love this scenery and that’s a good thing, because truth be told, the wait can be long at times.  Also, in town, the Chatham Cookware Cafe is the spot for great coffee and breakfast sandwiches.

Lunch: Chatham Squire.  This is the more famous Chatham outpost that everyone needs to check out.  “The Sqyya” as pronounced by some locals is filled with all aspects of Cape life.  From the license plates and the undergarments hanging above the bar, to the staff that have been there for decades, this place will not leave you bored.  The menu serves up your typical seafood specials but the tavern menu does offer a chicken finger basket that will leave the kids coming back for more! And you must visit at night…the bar gets hopping…complete with intoxicated wedding party attendees to even more intoxicated fisherman to the college summer crowd (yes, intoxicated) and of course a Jukebox that makes the night even better…you need to experience the Squire during the day and night!

Dinner: Impudent Oyster.  You are on the Cape, eat some seafood.  Impudent has what you need.  A Classic.  We also love Bluefins right on Main Street which is the closest you will get to a NYC scene in Chatham, MA and has delicious sushi and drinks.


White Marlie:  A shop on Main St. that offers great beach essentials- from hoodies to kids swim trunks to worn-in T’s.  White Marlie is a sort of surf brand meets prep all rooted in Cape lifestyle.  A must visit.

Chatham Candy Manor: An iconic mainstay to Chatham, complete with the pink awning and creaky old hardwood floors.  All children need to visit, and will likely never stop talking about it.  From penny candy to fudge, this place is heaven for all.


1.) Cape League Baseball.  In a nutshell, the best college baseball players come to the Cape to play during the summer in the Cape League.  The Chatham A’s have a beautiful baseball field and the ambience is like no other…you think you are in a movie, maybe even Summer Catch.  It is dreamy summertime fun where you get to watch top level baseball, and the kids get to chase foul balls and play on the gigantic playground next to the field.  Honestly, it doesn’t get much better.

2.) Lighthouse Beach.  An icon to Chatham.  A picturesque lighthouse sits atop the beach, while the beach provides tons of beautiful sand and amazing views.  Okay…Hip Daddy likes to be true…this beach is famous for some of the wrong reasons.  Sharks have been spotted off the shores in recent years.  But have no fear, the town is on it, and swimming is safe unless the numerous spotters say otherwise.  That said, so it may not be the best place to swim, but it is a beautiful beach worth enjoying!  For those of you who who are not Great White fans, drive over to Hardings Beach…

3.) Chatham Band Concerts.  The most amazing quintessential thing going on in New England every Friday night during the Summer…sound exciting?  Set your chairs up early in the day, and get ready to do the ‘Bunny Hop’…the Band Concert might just be the coolest Hip Daddy Approved Summer experience ever!

Okay, that’s about it.  Chatham is the place to be come Summertime.  Hands down, it is THE Cape vacation you have been dreaming about.  Perfect for the families, Chatham is the ultimate Hip Daddy Travel location.