Winnetka is home to pristine beaches, tree-lined streets, picturesque parks and a variety of destinations for shopping, dining and entertainment. We’ve compiled our picks for the best spots to dine, shop and visit when passing through one of the North Shore’s most scenic neighborhoods.
Where To Eat
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64 Green Bay Road, Winnetka / Website
Contemporary French-American eatery Aboyer serves indulgent, globally influenced fare like housemade charcuterie boards, escargot bourguignon en croûte and ragout of lamb tagliatelle. Pair your meal with beverage offerings like sparkling, red and white wines, Sparrow coffees and herbal teas.
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501 Chestnut St., Winnetka / Website
Located on the corner of Chestnut and Oak Streets, this neighborhood restaurant introduces a curated selection of wine, craft beer and signature cocktails, accompanied by tasty menu staples like lobster and mascarpone ravioli, short rib beef bourguignon and roasted spaghetti squash pasta with arrabbiata sauce. Helmed by owner and restaurateur Mark Salmon, the dining destination has recently been named a 2024 Open Table Diners Choice Award winner, recognized for its high-caliber dining experience.
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844 Spruce St., Winnetka / Website
With a spacious dining room, a bar, a sidewalk cafe and a garden courtyard, this French restaurant offers daily dinner service and weekend lunch and brunch—from pan-seared foie gras to Florentine crepes with spinach and Camembert cheese. Amp up your dining experience with Pomeroy’s selection of desserts and aperitifs like Calvados La Pommière, assorted macarons and the Plateau à Fromage, an array of artisanal cheeses, marinated olives, honeycomb and walnuts.
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924 Green Bay Road, Winnetka / Website
Spirit Elephant is the first entirely plant-based restaurant and bar on the North Shore, offering vegan and vegetarian alternatives to your favorite comfort food staples. Start small with the tomato-topped Toro nigiri or the cauliflower ceviche, or go all in with fresh pesto zucchini spaghetti or pad Thai with pan-seared blackened tofu.
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507 Chestnut St., Winnetka / Website
Owner Bruno Abate brings authentic Italian cuisine with a modern twist to the North Shore at Tocco, home to small bites, pizza, handmade pasta, meat and seafood that make the cut. For the full experience, try the pan-seared Chilean sea bass with crustacean sauce and potato puree, the Pappardelle Alla Norcina with Italian sausage, black truffles and cream and the Tagliata grilled New York strip steak.
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921 Green Bay Road, Winnetka / Website
Cafe and private event space Towne & Oak’s selection of grab-and-go items and made-to-order fare like salads, tartines, cheese platters and daily specials is not to be missed. Swing by the eatery to refuel on drip coffee, lattes and espresso shots or start your day with crave-worthy cuisine like croissant breakfast sandwiches, butternut squash tartine and smoked salmon pate on griddled country bread.
Where To Shop
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555 Chestnut St., Winnetka / Website
This luxury boutique features womenswear, shoes, accessories and home goods from notable designers like Free People, Agolde, Ganni, Veronica Beard and more. The chic storefront features the latest staples, from seasonal dresses to evergreen denim essentials.
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874 Green Bay Road, Winnetka / Website
Closet curator Melissa Carter owns and helms this vintage shop, home to a vast collection of high-quality preloved statement pieces like womenswear, accessories, outerwear, menswear, dresses, jumpsuits and more. Fashion enthusiasts can expect expert creative direction and personalized styling services from the boutique’s team, who strive to help each client hone in on personalizing their wardrobe.
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912 Green Bay Road, Winnetka / Website
Twenty-two years ago, North Shore native Lana Bramlette founded her designer line, Lana Jewelry. Shoppers can now find the brand’s 14-karat gold pieces and diamond-studded staples at Neiman Marcus, Bergdorf Goodman, Nordstrom, Saks and Lana Jewelry’s Winnetka flagship. Visit the shop to peruse jewelry pieces, including earrings, necklaces, rings, and bracelets.
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735 Elm St., Winnetka / Website
Elevate your living space with the latest home decor finds from this high-end lifestyle retailer. Shop for pillows, throws, furniture, lighting, gifts and more, expertly curated by Maze’s expert team, helmed by owner and interior designer Cindy Bardes Galvin.
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560 Chestnut St., Winnetka / Website
Fashion retailer Neapolitan Collection’s expansive showroom is filled with ready-to-wear, shoes, accessories and jewelry from top global designers, sourced straight from the runways of New York, Milan and Paris. Owner Kelly Golden travels the world to bring cutting-edge statement pieces from fashion houses like Dior, Fendi, Valentino and Prada to the North Shore.
What To See & Do
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899 Sheridan Road, Winnetka / Website
This scenic beach runs along Lake Michigan and gives visitors premier access to a beach house, pier fishing and beach-season lifeguards. Bring an umbrella and snag a seat on the sand to take in picturesque lakeside views, all while soaking up the sun.
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895 Green Bay Road, Winnetka / Website
Whether you are looking for a new mantle statement art piece or some conversation-starting wall decor, this art gallery is one to visit. Peruse the showroom’s vast selection of paintings and photographs with over 20 artists exhibited daily.
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754 Elm St., Winnetka / Website
Winnetka Farmers Market is the perfect place to shop for produce, florals, bakery items and artisan goods from over 114 local farms and businesses. This year’s vendors span Kugel Farms, Karmen Family Creations, Café Fleurette, SkyFall Flowers, Great Harvest Bread Company and more. For more information regarding hours and seasonal availability, visit the Winnetka Farmers Market website.
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1300 Oak St., Winnetka / Website
This famous golf club features a championship 18-hole golf course, a par-3 nine-hole golf course, a driving range, practice greens and a clubhouse with a pro shop for food and beverages. Visitors can step up their game with lessons for juniors and adults or join for the latest events and club meets.
See also: The Ultimate Guide To Highland Park
Photography by: Tim Abbott / Getty Images / iStock Photo
