Winnetka Family Guide! | Chicago North Shore Moms

Winnetka Hot Spots


This guide was updated in 2024. This charming village may have been made famous by Home Alone, but that’s just a tiny part of what makes this village amazing! Winnetka has distinct business districts & each is is filled to the brim with wonderful shops and restaurants, not to mention the parks and beaches sprinkled through each.



Winnetka is home to some really cool shops, restaurants, cafe’s and parks. Hubbard Woods has some of the chiquest couture shops as well as interior design studios for all of your design needs. Elm Street business district has an East and West side that stretches right across Green Bay Road. East Elm can be reached from the Green Bay Trail by bike, and has become a common biking destination because the ultra family fun businesses all within one strip of adorable brick buildings. Shopping for home and gifts is also a common stop here with easy parking and a a favorite coffee stop here to boot.


East Elm Street District

Beat Street Toys is packed to the brim with the most creative selection & my kids could spend hours just looking through the owners carefully curated selection! And located in the same mini-mall is Games on Lincoln, an old skool arcade with hours after 3pm.

We also love neighboring Bashy Bash for mini-piñata’s and party supplies.  Tip- the mini-piñatas make the cutest kids gift when stuffed with little candies and trinkets (from Beat Street right next door for kids, and with a gift card/jewelry/lip balm, etc for adults)!  It’s now my go-to fun gift.

Maze and Mandarin Home are both found on this block and can fulfill all of your North Shore home vibes with preppy and classic accessories and gifts.  Tip- the monogram services at Maze are quick and fantastic for baby, little travel bags and more for friends, and wedding gifts!

The added bonus to this area- parking is easy and the shop owners are all incredibly sweet!  Also, Indian Hill park is a short walk/bike/ride away from East Elm with a large play structure and green space.  This is our usual next stop after ice cream at Mitch’s!

Hungry for more than sweets? Across the street you’ll find Hometown for coffee, juice and tasty, but healthy eats, and Stacked and Folded for to-go tacos, and more (The quesadilla is a favorite! I don’t know how they make it so crispy, but it’s too good).



West Elm Street District

West Elm Street District always feels a little fancier to me & where I visit when I want to actually change out of my yoga pants for a meal, or really treat myself shopping.

Bunny & Babe womens boutique is curated so well & the decor is so cute and fun it just makes you want to shop!  (It’s a problem. lol)

Valentina is filled with a great mix of high and low, and a go-to for good denim. You can also find a fun assortment of gifts here and even home accessories.

Evereve is another great and more affordable clothing shop, now located in the heart of West Elm Street District.

When with the kids, a stop in The Book Stall is usually a hit.  You can never have enough kids books!

Dining is hot with Pomeroy! This hotspot is pretty, yet comfortable and the food is delish and you must dine on the outdoor patio space when weather permits. There’s a reason it’s tough to get a reservation!

And you simply must make a stop into Good Grapes to get wine pairings from owner, Theresa. The shop is adorable, features wine tastings weekly and has a fabulous summer series when weather permits.

Fred’s Garage is our other standby in the area with the kids, for patio days, after sports, live music nights without the kids- you name it, you’ll find us here at least once most weeks.

We love La Taquiza just across from Fred’s for good mexican take out, & the margs and micheladas are fab as well.

Understated is Green Bay Cafe, a cute (very small) and very good cafe located caddy corner to Fred’s. Cash only here.

Noah’s Ark is where you can pop in to treat the pup! Follow up a visit with coffee from Pete’s and a stop at Dwyer Park just across on Birch Street.

We don’t visit the beaches in Winnetka as often, but there are many. Like most North Shore beaches, daily and season passes are cost prohibitive to nonresidents. Winnetka pricing a little friendlier than some!  Tower Beach is a favorite with a play structure and wide stretch of sand. Elder Lane Park and Beach is wonderful for the kids (it was closed all of 2023 due to water levels), the play structure over looks the water and has a large grassy area to run, and Centennial Park next door is a great place to mingle.



Hubbard Woods District

Hubbard Woods feels like an entirely new village as you make your way there north on Green Bay Road from the Elm Street business district. This cute strip of shops, galleries and restaurants feels more casual than its neighbor, but is still bustling- Especially since Towne and Oak hit the scene!

This area has one of the cutest train stops (Hubbard Woods) with a park complete with a play structure, splash pad, and an area that serves as a stage through the warmer months!  We love visiting Graeter’s Ice Cream on warm days and walking across the street to enjoy the park after!

The above mentioned Towne and Oak has become a breakfast and lunch favorite with one of the best egg sandwiches we’ve ever enjoyed and all-around good food in a beautiful space.

Grateful Bites Pizza, just next door on Green Bay, is also one of our very favorite options not only in Hubbard Woods, but in the north shore.  Their unique pizza combinations are delish.

Spirit Elephant is a popular vegan restaurant, with tasty cocktails, a bright, pretty interior, and a cute patio to enjoy come summer! *You don’t have to be vegan to enjoy the food!

If you like margaritas & good mexican Guanajuato is a must.  This unassuming location is pretty and cozy inside, with the best food and drinks.  The ceviche tostadas + a spicy marg are one of my favorite meals in the North Shore.

Next to Guanajuato is Green Bay Bikes, for all your biking needs with the friendliest owners and staff, and right across you’ll find Randoons for comfy clothes to do everyday mom-life in. This has become my place to pick up new band tees for both me & the littles, and she has a great selection for kids & gifts.

Another understated brunch spot in Winnetka is Momsy’s Cafe, home to an amazing tuna melt and many other fine sandwiches and home-baked goods. This spot is pretty quiet so it’s actually a great place to meet up with a friend or colleague without too many distractions.


Towne & Oak, Winnetka


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