I grew up within walking distance of a town so small that I only had to give my last name to any shopkeeper and he would put my purchase on a house charge. That’s what my longtime adopted hometown of Rye feels like—a throwback to the idyllic burg of my childhood. Forget soulless strip malls and cookie-cutter chains: Picture-perfect Rye is made for browsing, and it’s an ideal spot to while away a fall day. You’ll want to soak in the preppy vibe: Imagine a year-round Southampton, complete with a small shopping district, plus stunning shoreline vistas, parks, and beaches not far from town.
At six square miles, Rye is technically a city (the smallest in the county) but it feels like a quaint village. Start by heading to the main shopping area along the appropriately named Purchase Street. Fuel yourself with a cappuccino and slice of fresh-baked apple strudel at the elegant Patisserie Salzburg—Meryl Streep filmed here for the movie Ricki and the Flash—then set out to explore.
Everywhere you turn, there’s a carefully curated boutique, one-of-a-kind shop, unique gallery, or gourmet eatery—often located in a historic old building—just waiting to be discovered. Do stop into Angela’s for sophisticated, high-end women’s designer labels; Walin & Wolff for high-fashion footwear and luxe leather goods; and Twish for exquisite clothing for the little ones and home gifts (most can be monogrammed).
Nest Inspired Home
Other standouts include Nest Inspired Home for “classic contemporary” furnishings, lighting, and accessories that are modern but not overly trendy and Parkers is great for unusual travel-related items. And don’t miss family-owned R&M Woodrow Jewelers for a handsome collection of internationally acclaimed designers, such as Italy’s Roberto Coin and Buccellati.
Take a break from all that browsing and buying by picking up a gourmet picnic lunch at longtime favorite Rye Country Store. Then chill out at nearby Rye Town Park, a lush oasis with a sparkling beachfront, rolling acres of lawn, and a duck pond. Stroll the boardwalk or simply plant yourself on one of the many benches and drink in the views of the sea—and on weekends, lots of Vineyard Vines-like frolicking Labs, Goldens, and such.
Longtime favorite Rye Country Store
As the day winds down, head back to town for dinner. Choose from among an excellent French bistro (Encore Bistro Français), a seafood restaurant (Morgan’s Fish House), a steakhouse (Frankie & Johnnie’s), or a pizza parlor (Sunrise Pizzeria), some with cafe-style outdoor seating. Or simply kick back with a cocktail on the inviting front porch of The Rye Grill & Bar and toast your newest happy place, Rye.