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A local mother and daughter explore five hidden areas around Chatham dressed in classic and colorful clothes from Sara Campbell, Chatham Clothing Bar, Lily Pulitzer, The Trading Company and If the Shoe Fits

Library at Chatham Bars Inn

Amidst the bustle of the grand lobby of Chatham Bars Inn, nestled off the elegant main seating area, is a cozy and charming library. With a decorative fireplace, floor-to-ceiling books and plenty of board games, this nook is ideal for a quiet retreat during your visit to this venerable resort. You can even bring your coffee, tea, cocktail or glass of wine—served in the adjacent South Lounge—with you as you snuggle up with a good book on a wintery afternoon.

On Jillian: Tonet two-piece dress plisse skirt and sweater with paillettes, Columbo Cashmere/silk accordion pleated scarf, Fabiani Filippi Taupe cross body leather bag with Monili silver trim and Brunello Cucinelli mixed metal bracelet.

On Lori: Loro Piana Buff Cashmere basket weave sweater, Loro Piana Paper Bag Cashmere pant, Loro Piana cream double-faced Cashmere wrap with fringe and Fabiani Filippi gray satchel with Monili silver trim.

Outfits are available at: Trading Company
614 Main St. 508-945-9191,

Packet Wharf

Dotted with old sea captains’ homes, Water Street runs from Mill Pond to the Atlantic Ocean, where it was once an important part of the commercial center of Chatham. In the 1800s, this now-quiet Town Landing was abuzz with Boston-bound packet ships unloading both passengers and cargo at wharves that jutted into the harbor. It’s best to get here on foot, as there is limited parking on this street.

On Lori: Cashmere/wool blend ribbed sleeve open cardigan paired with essential Sheri Pants.

On Jillian: Short sleeve rouched turtleneck with a colorful tweed skirt and resin chainlink statement necklace.

Outfits are available at: Sara Campbell
578 Main St. 508-348-1702,

Enchanting Courtyard

Tucked between Main Street’s Lily Pulitzer store and the Snowy Owl Espresso Bar, this shaded and charming courtyard is a perfect place to stop and enjoy a cappuccino in the middle of a busy mother-daughter shopping day. Relax at one of the many tables or unwind on one of the benches set amongst trees and greenery.

On Lori: Elsa silk blouse in true navy with Kelly high-rise skinny ankle pant in Zanzibar zoo and Malindi clutch in gold metallic.


Featured bracelets from Lilly Pulitzer’s jewelry collection.


Shoe: Bridgette wedge in gold metallic

On Jillian: Sleeveless Emile dress in Zanzibar zoo, paired with Terri wrap in heathered blue peri, with starfish charm and short necklace from Lilly’s resort charm bar collection and Sirena Crossbody in Gold Metallic.

Outfits are available at: Lily Pulitzer
483 Main St. 508-348-0106,

Godfrey Windmill

Originally located on Mill Hill east of Atwood Street (now Stage Harbor Road), this circa 1797 wind-powered grist mill, built by Colonel Benjamin Godfrey, was moved in the mid-1950s to the newly designated Chase Park, a small and secluded park off Cross Street that was donated by Avis Chase. Over the years, the Godfrey Windmill has undergone significant renovations that were ultimately completed in 2012, in time to celebrate Chatham’s tri-centennial. Open seasonally for tours and corn-grinding demonstrations, the windmill is a wonderful year-round spot for a dog walk or a stroll with friends and family.

On Jillian: Ost camo jacket, Ost turtleneck, Roxy skirt and Tey-Art belt

On Lori: Ost reversible jacket, Ost turtleneck, Tey-Art belt, Not Your Daughters white jeans and Joy Susan hobo bag

Outfits are available at: Chatham Clothing Bar
534 Main St. 508-945-5292,

Little Mill Pond

This saltwater pond, located just south of Main Street and west of School Street, allows access to Nantucket Sound via Stage Harbor, making it a popular location for residents of nearby Mill Pond Road, Chase Street and other local neighborhoods to moor their boats.

On Lori: Aldo Martin Shawl Collar Coat, DL 1961 Florence cropped jeans, Rosemunde cotton/silk turtleneck, Soft Shoe Bellis bootie, Amsterdam heritage leather belt. Latico cross-body bag.

On Jillian: DL 1961 Ultra high-rise skinny jeans, Mauritius Christy Stars leather jacket, RD style sweater and Eva Hike Hiker bootie.

Outfits are available at:  If the Shoe Fits
442 Main St. 508-348-1926,

Special Thanks

Special assistance from:
Alex Hillman, Kaytlyn Kedmenec, and Rebecca Tadema-Wielandt


Oasis Salon & Day Spa
1671 Main St., 508-945-5577,

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