Harry Maisel Blog

Welcome home to Winnetka

Greenery galore is what you will see in Winnetka. The mature trees, access to fantastic Lake Michigan beaches, large acreage of public parks and walking and biking trails including the Green Bay Trail are what make Winnetka a place to always be active. I enjoy spending time in Winnetka because it’s filled with some of my favorite restaurants in all of the north shore. And Winnetka has two retail districts, one in Hubbard Woods (several scenes from the John Hughes movie “Home Alone” filmed here) and the other retail area in downtown Winnetka in and around Green Bay Road and Elm Street. Dotting the streets in these areas, are a variety of Café’s, specialty gift stores, bookshops, medical service providers

Among these two retail districts, there are two convenient Metra train stations that will take you directly into Chicago.


Fun Facts

1.  What do these Hollywood Icons all have in common: Rock Hudson, Ann-Margaret, Charlton Heston, and Bruce Dern? They are all famous actors that came from New Trier High School in Winnetka. New Trier High School officially opened its doors in 1901.

2.  Picture Lollapalooza for grown-ups and you get The Winnetka Music Fest. For the last 6 summers; Winnetka, Winnetka Park District in conjunction with Val Haller, CEO/FOUNDER of VALSLIST music produces a unique summer music live experience featuring the best emerging new musical artists situated in downtown Winnetka.



Fitness and Outdoor Recreation

 1. CorePower Yoga located at 850 Green Bay Road in Winnetka is a dynamite spot to get hot and sweaty while working on improving your yoga practice. Conveniently located on the corner of a strip center that offers ample parking and a McDonalds for an after-workout snack. https://www.corepoweryoga.com/yoga-studios/IL/Winnetka/winnetka

2. The Winnetka Community House is situated at 620 Lincoln in downtown Winnetka, and it is run by the Winnetka Park District. This facility offers everything under the sun but many who live in Winnetka don’t take advantage of the array of activities and programs. The fitness facilities here include group exercise classes from Flow yoga, HIIT, Shred, Full body Barre, Upper body burn, strength and cardio, Latin remix and more. You can take individual classes for $15, or they offer three different types of memberships from $59 and up. For the $99 a month membership you’ll get access to free child day care while working out, Peloton experience studios which offer a private room to do a Peloton class in and the ability to use a Hydro Massage Chair post workout.


3. The Green Bay Trail -Just east of Green Bay Road there is a ravine that surrounds Metra trains that go to and from Chicago. Alongside this train line runs the Green Bay Trail. The trail is built on former Milwaukee Railroad trainline and extends for nine miles. All year round you’ll see runners, walkers and bicycle enthusiasts get their steps and bike miles in.

4. A.C Nielson Tennis Center-530 Hibbard Road in Winnetka. Offering eight indoor and twelve outdoor tennis courts (5 night lit), professional instruction, league play, and multiple paddle tennis courts (platform tennis) and fall/winter men’s and women’ leagues. Next door there is an 18-hole golf club, pro shop, and next door to that is the Winnetka Ice Arena for hockey/ice skating.


Best Spots to Take Your Instagram Selfies

 1. The Bocce ball area in Hubbard Woods Park right across from Mino’s restaurant is a great place to play a fun old school game and take a few photos and have a park setting in your camera’s background.

2. Kevin McCallister’s parent’s home in the movie “Home Alone” is a few blocks from downtown Winnetka. Each year tens of thousands of people flock here from all over the world to take selfies in front of this iconic house. In real life, the home has sold well over the two-million-dollar mark.



 1. Pomeroy is one of the hottest new restaurants in Winnetka. This French fare bistro that features a massive square bar in the center of the space rivals any cool Chicago city bar. If you want to be seen, make sure you look your best here. The food served here is smaller in size but the attention to detail and quality is what you’ll experience.

2. Born in Naples Italy and raised in Milan, Bruno Abate was inspired at an early age by his parents for his passion in food and fashion. Bruno took this expertise to Winnetka to open Toco located at 507 Chestnut across from the Winnetka US Post Office. Simple fresh Italian food that is simply delicious. You’d think you were transported to Italy with the variety of delicious pasta, antipasti, chicken, meat, and fish dishes. An array of Italian desserts will round out your meal During the middle of Covid I had the opportunity to take a zoom cooking class with chef Bruno. He led a class on making sauce from scratch using the best quality ingredients and when it was done it tasted unbelievably delicious. https://tocconorth.com/

3. Sunday brunch anyone? If you want a bagel, lox, and cream cheese, you’ll find it at Once Upon a Bagel located at 1050 Gage Street in Winnetka. A full menu of outstanding deli food includes an array of omelets, pancakes, gourmet corned beef and pastrami sandwiches, homemade cream cheese in all varieties, bakery items and of course Matzah ball soup.



Fun with Kids

1. The Skokie Lagoons is located on the west end of Winnetka right off Tower Road and Forest Way. In the summer you can rent canoes and kayaks where you will be able to glide through the lagoons and view the beautiful area forest preserve.

2. The Winnetka Community House offers a huge assortment of kids’ programs that include a myriad of youth sports, musical theater performance, dance, marital arts, STEM classes, arts, and crafts and so much more.

3. Centennial Dog beach is an off-leash swimming beach located on Lake Michigan in Winnetka. It’s the perfect place for your four-footed best friend to get some exercise, go for a swim, or just have some fun. The beach is open from dawn to dusk throughout the year, weather permitting.



1. Looking for one of the best mani-pedis? Head over to Oak Spa Nails at 916 Green Bay Road in Hubbard Woods/Winnetka. Featuring a very modern/cool light vibe environment, this salon is open 7 days a week.

2. The Massage Therapy Center of Winnetka has consistently been rated as being the best massage on the north shore according to Make it Better Magazine and the Chicago Sun-Times. Offering Swedish, Deep Muscle, Shiatsu, Sports, Pre-natal and other forms of massage will provide restorative healing to your joints and muscles.


3. Looking for the best in hair care. Look no further than the Paul Rehder Salon in Winnetka. With amazing reviews and located at 952 Green Bay Road in Hubbard Woods/Winnetka, the minute you walk into the cool interior of this space, you’ll feel a sense of calm. Offering the best in women and men’s hair treatments that include cuts, Keratin treatments, highlights, custom color, Japanese straightening, and express blowouts.




 1. Serena and Lily is a home design store located in some of the most affluent towns in the US so it’s no exception that they would add a beautiful brand-new store in Winnetka’s Hubbard Woods shopping district. This hi-end home store offers gorgeous bedding and linens, furniture, stylish lighting and décor, nursery, kids’ furniture and much more. This boutique store will be one of your favorite stops when you move into your new home here.

2. Can you say “Score”? The Winnetka Thrift Shop is not your ordinary thrift store. Located at 992 Green Bay Road, this store is a rare and great find. Every week new items are put on the sales rack including high-end brand-named clothing and accessories. Pick  up a real deal for yourself or your friends and family.


3. Neapolitan Collection located in downtown Winnetka is dedicated to offering the most luxurious collection of international fashion. Yes, this exclusive women’s store is uber pricey but then again you don’t have to travel to Paris or Milan to acquire your dress because Neapolitan offers the best of the best right here.




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