What You Should Do to Get the Most Out of a Weekend in Chatham

Chatham is one of the most iconic areas on the Cape. Whether you are looking to relax on Lighthouse beach or be a part of the exciting atmosphere the local restaurants have to offer, we have you covered. We created an itinerary with helpful suggestions to make the most out of your visit to Chatham.

Day 1 in Chatham: Self-care and Delicious Food

What better way to truly enjoy your vacation by starting it off with a relaxing spa trip to Chatham Bars Inn? Located at 297 Shore Road, the spa offers the finest in luxury treatments and amenities. Guests that are 16 years of age or older can rejuvenate at the spa and restore the mind, body, and soul with the different services offered at this lavish scenery.


Once you have set the tone for your Chatham get-away, be sure to stop by Chatham Fish and Lobster at 1291 Main St. Whether you are craving seafood, sandwiches, or appetizers and drinks, the Squire has it all just a quick walk down the road at 487 Main St.


You'll want to save room for dessert for your walk home as you will pass Buffy’s Ice cream shop for some delicious home-made ice cream. What better way to end your first day in Chatham than watching the breathtaking sunset at the famous Lighthouse Beach that is just a quick 10 minute walk from the house.

Day 2 in Chatham: Sailing and Beach Sunset

Start your day off right with a trip next door to Snowy Owl Espresso Bar at 483 Main St. for your choice of coffee, espresso, or tea. Once you have picked up your delicious morning coffee, head back home to your cozy front porch. Nothing will beat the fresh morning air, a cup of coffee, maybe a book, and admiring the Chatham locals making their way to the beach. Get ready for one of the most memorable experiences you will have on the Cape with Cape Sailing Charters at 613 Stage Harbor Rd. Spend your late morning/afternoon on the beautiful waters that are known as the "perfect port from which to sail." Whether you are just planning on a leisure afternoon trip with your family or a magical sunset cruise, Cape Sailing Charters will give you a memory that will last a lifetime. Once this exciting sailing trip comes to an end, finish this beautiful day at Hardings Beach by admiring the stunning sunset with your friends and family. Then, head back home for an easy clean up in the spacious outdoor shower and create those unforgettable memories with your favorite people by the beautiful fire pit.

Day 3 in Chatham: Shopping and Photography


Take advantage of the luxurious kitchen and large island countertop and cook up a breakfast buffet to enjoy with the family. Be sure to head to the well-known Main Street shops to treat you and your kids to some Chatham goods. Treat you and your kids at The Candy Manor where you can buy homemade fudge and delicious sweets.




After an exciting day of strolling through the shops and restaurants of Main Street, stop by the favored Chatham Squire. Whether you are craving seafood, off the grill, sandwiches, or appetizers and drinks, the Squire has it all for an enjoyable lunch and dinner just a quick walk down the road at 487 Main St Head home and enjoy your food in the comfort of the Priscilla House backyard. Once you’ve filled up on some comfort food, take a 10 minute stroll down the street to the beach. There is no better way to wind down and end your day by watching the sunset on Chatham Lighthouse Beach. Capture these precious moments with award winning Kristen Deem Photography for a beautiful professional photoshoot on the beach. Admiring the gorgeous view of the sun setting below the 200 year old Lighthouse will be one of your favorite parts of your unforgettable trip to Chatham.


If you are planning to stay out late for drinks with the adults, book with Summer Sitters that will have an experienced, responsible, and CPR certified babysitter come to the house and make sure your kids are safe and entertained.


Get Acquainted With Your Chatham Rental Home


Our partner, New England Vacation rentals offers The Priscilla House in the heart of Chatham. This particular rental is in an ideal location for quick and easy travel while also giving you the option to stay put and enjoy some time in a beautiful, traditional Cape Cod backyard. This luxury-styled home has nine bedrooms, central A/C, a washer and dryer, and gorgeous living rooms with flat screen televisions. The rental also includes bed linens, bath towels, beach chairs, beach wagons, an outdoor shower and plenty more.


Priscilla's private backyard is the exact scenery you want for a catered clam bake or family cookout. Avoid the stress and ask Down the Cape Concierge to assist planning a backyard clambake for your family or friends. The yard itself is perfect for your kids or pet to safely run around and enjoy those ideal summer nights on the cape that they will cherish forever. Enjoy an iconic Cape Cod cookout with the outdoor grill setup, and then relax by the fire pit with a delicious cocktail for the adults and s’mores for the kids.





Cook a mouthwatering breakfast buffet in this spacious kitchen with all stainless appliances. Then, you can get ready for your beach day by gathering around the centered quartz kitchen island for sandwich prep. Even with a lot of friends and family, you'd never feel crammed in this house as there is plenty of space and comfortable seating starting, including a 12-16 person dining room table!

Let's Plan Your Chatham Vacation!

We want to make sure you and your family have an exciting, stress-free, and memorable vacation. Chatham has everything you need to relax, explore, and make those precious summer memories with your loved ones. We can provide you with any services you may need during your Cape Cod vacation.


If you are a New England Vacation Rental guest, you can download the Happy Stays X app on Apple or Android for more on how to spend your time in Chatham. If you are interested in renting The Priscilla House, send an email to atyourservice@downthecapeconcierge.com.