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November 22nd, 2021

Holiday Shopping Guide to Chatham's Main Street


Shop ‘Til You Drop on Chatham’s Main Street This Holiday Season

By Colleen Blair, @travelikealocalma


With the holiday season upon us, there’s no better time for a stroll down Chatham’s Main Street to find the perfect gift for everyone on your list. With the Chatham Wayside Inn located in the center of town, right in the midst of the action, it’s the ideal place to stay during a holiday visit to Cape Cod.


Whether you’ll be in town for Chatham’s “Christmas by the Sea” Stroll Weekend (Dec. 10-12, 2021) or are simply planning a pre-holiday getaway, I’ve included a list below of 10 of my favorite can’t-miss local shops for holiday shopping on Chatham’s Main Street.


All of the shops within are just a quick stroll from The Chatham Wayside Inn (no driving required). After you shop ‘til you drop, head to The Wild Goose for some Goose Fries and a delicious meal. Or grab a holiday-inspired cocktail at the bar and enjoy the Inn’s festive yuletide décor.


Artful Hand Gallery

With a focus on American craftsmanship and innovative design, Artful Hand Gallery offers one-of-a-kind gifts to please even the most difficult gift-recipient on your list. From a stunning selection of handmade and designer jewelry, to art by local New England artists, to objects for the home, you’re bound to find something you’ve never seen before, making for thoughtful and fun gift giving. 459 Main Street, Chatham, MA


Chatham Candy Manor

Whether you’re looking for stocking stuffers, hostess gifts or just some sweet treats, the Chatham Candy Manor has you covered! From their delicious homemade candy canes, seasonal chocolates and truffles, to nostalgic retro candy (think Pop Rocks, Ring Pops, and Airheads) you can find it all at the Candy Manor. Look out for their signature pink awning on Main Street, and prepare to satisfy your sweet tooth. 484 Main Street, Chatham, MA


The Chatham Home

The Chatham Home is full of exquisite gifts for anyone on your list who loves décor and design. From luxurious Matouk linens and throw blankets, to Jill Rosenwald ceramics, to LAFCO candles and diffusers, to AERIN vases and bowls, The Chatham Home carries the best of the best for those on your list with impeccable taste. 443 Main Street, Chatham, MA


Ducks in the Window

Ducks in the Window_Holiday

Perfect for both the young and the young at heart, Ducks in the Window is a Chatham icon and the world’s largest retail rubber duck shop. They offer a great selection of holiday ducks (perfect for the kiddos, or anyone who likes to enjoy a long, hot bath), along with bath bombs, puzzles and toys and games. It’s not a trip to Chatham if you don’t leave with a new rubber ducky! 507 Main Street, Chatham, MA


Gustare Oils & Vinegars

Featuring artisan extra virgin olive oils and balsamic vinegars, Gustare Oils & Vinegars is the perfect place to find a hostess gift or a gift for the chef in your life. The owners couldn’t be more lovely, and they’ll be happy to help you find the perfect pairing of olive oil and vinegar, along with other regional gourmet food products. Their gift sets and gift boxes are perfect for holiday giving. 461 Main Street, Chatham, MA


Mahi Gold

Known for nautically-inspired prints and comfortable, flattering fabrics, Mahi Gold offers dresses, tunics, tops and more, sure to please anyone who loves Cape Cod style. Featuring fun and colorful prints in both Coastal Cotton and nylon Chatham Cloth, Mahi Gold offers some of the most comfy and stylish looks in town.  465 Main Street, Chatham, MA


The Mayflower

Mayflower Shop_Holiday Cards

The Mayflower Chatham is a whimsical shop on Main Street, selling everything from gifts and décor, to an amazing selection of greeting cards, to toys and games for children. With a coastal chic aesthetic, you’re sure to find gifts for anyone who loves the beach. 475 Main Street, Chatham, MA


Sundance Clothing

Known for their best-selling cozy fleece-lined leggings, Sundance also offers the latest styles of sweaters, jackets, tops and accessories for women. They have a wonderful selection of festive Wooden Ships sweaters, and the comfiest Hello Mello loungewear – just what I’d love to find under the tree this year. 497 Main Street, Chatham, MA


Tale of the Cod

Tale of the Cod_Holiday

Offering gifts, furniture and home accessories, Tale of the Cod carries beloved brands including Mariposa, Simon Pearce, Dash & Albert, Scout Bags and much more. Along with gifts, you’ll find gorgeous decorative pillows and cozy throws, as well as items like fun cocktail napkins and place setting ideas for your holiday get-together. 450 Main Street, Chatham, MA


Yellow Umbrella Books

I can never resist a local bookshop, and Yellow Umbrella Books is no exception. From recent bestsellers, to books by local Cape Cod authors, to tomes about Cape Cod and the surrounding area, you’re sure to find something you want to read when you step inside. Take the time to browse and ask for recommendations – the staff is always ready to help you choose a book for yourself or to give as a treasured gift. 501 Main Street, Chatham, MA


Want more ideas for visiting Chatham in the winter? Check out the Inn’s latest blog post on winter activities in the area!


Colleen Blair is the Boston-based content creator behind @travelikealocalma, where she documents her travels and provides recommendations for things to do and places to explore in Massachusetts and throughout New England. She loves visiting Cape Cod year round – especially Chatham – and is an advocate for shopping small and buying local.

"The Wayside Inn is our little piece of heaven when we need to have a little bit of downtime. It is heaven on earth. The food is delicious and the staff extraordinary. They have become like a family to us. We would recommend The Wayside Inn to anyone looking for a special place to stay on Cape Cod. You will not be disappointed."

Patricia Abroderick, May 2022, Trip Advisor

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"When I hear continental breakfast I don’t think of the outstanding breakfast they offer! Top notch breakfast, exquisite dinner, and the location is perfect! Excellent friendly housekeeping and quiet comfortable rooms! Couldn’t have been happier!"

Expedia Reviewer

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"The charm of the facility and the friendliness of the staff was amazing and we would definitely recommend this place and stay here again."

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