Browse the Directory

Highwood, Illinois - Community Info

To search for homes & condos in Highwood, try our free North Shore Chicago Real Estate Search.


Highwood, Illinois is a North Shore community with a colorful past. Many of the homes there were beautifully constructed by talented Italian stone and brick masons who settled in the area. The village is located at the top of the ravines in Skokie, making Highwood the highest spot between Milwaukee and Chicago.

Fort Sheridan, which closed in 1993, played a unique role in shaping Highwood. The Fort was known for the numerous bars that were in business there and garnered the nickname of Whiskey Junction. Highwood, which developed a similar reputation for drinking by association with the Fort, eventually decided to reinvent itself and urged those establishments to eliminate the liquor and focus on food. The plan worked and Highwood became well known as home to some of the best restaurants in the Chicago area.

Not only did Highwood relinquish its title in the Guinness Book of World Records for highest number of bars in one village, it also lost Fort Sheridan. But that loss turned into a gain for the community because the land and subdivisions of the Fort were annexed, allowing the village to double in size. With a current population of just over 4,000, Highwood is still one of the best places to go for great food on the North Shore.

A drive along Green Bay Road will take you to a number of fantastic restaurants in Highwood. Gabriel's Restaurant is also manned by chef Gabriel Viti and serves five course meals for an average price of $125.00. This French/Italian restaurant has outdoor seating available as well as private dining room. Reservations are recommended there.

For delicious Italian food, Alex's Washington Gardens is the place to be. It's said that Alex's started out by being the first to serve pizza on the North Shore in 1944. They progressed to adding a wide selection of Italian specialties to their menu and have been a local favorite for decades.

Yiannis Opa! Restaurant On Green Bay in Highwood serves authentic Greek food. They welcome families and even have live entertainment on scheduled evenings.

Del Rio Restaurant is another place that serves classic Italian, or if you prefer seafood then Bertucci's is a good choice. Froggy's French Cafe is of course mainly French cuisine and the Gourmet Frog Bakery & Gift Shop is next door to serve as a bakery and handle carry out orders. Gabe's Backstage Lounge, Pierantoni's (which has been family-owned for 54 years) and the Sage Grill round out the dining options on Green Bay Road in Highwood.

Moving on to Sheridan Road, the selection is no less impressive. Sandy's is a nice, family-oriented diner that serves traditional American food, along with other eateries such as Virginia's Restaurant Incorporated and Erik's Restaurant. The Nite 'N Gale is a bar and restaurant that has big screen televisions for customers who are sports enthusiasts and Buffo's has quick and friendly service. Some Italian stops on Sheridan are Olive's, La Strada Cafe, and Trattoria Giacomo Restaurant. Bacio Italian Deli offers a big selection of meats and cheese while Ferentino's is an Italian pizza place that also serves sandwiches and salads. Trattoria Giacomo only serves dinner, so plan on having at least one meal there. House of Peking specializes in Szechwan and Cantonese food while the Curry Hut serves Indian and Nepalese dishes.

Il Mulino Bakery is a Sicilian bakery offering wonderful authentic breads and desserts, and the Mocha Cafe and Wine Cellar is the perfect topper for an evening out in Highwood. They have a fully stocked expresso bar and can serve up any request. If ice cream is what you're craving, then Sweet Pea's Ice Cream Parlor will certainly satisfy. Sweet Pea's opened in 2003 but has quickly become a favorite dessert spot in Highwood.

Waukegan Avenue in Highwood has its share of fantastic restaurants. Miramar Bistro, Bar and Banquets in Highwood is run by chef Gabriel Viti and features a banquet hall that can be reserved for parties. The bistro is a combination of French and Cuban with a DJ every Friday and Saturday nights for dancing.

Fontana Di Trevi is an Italian restaurant that offers delivery, take out and catering. The Grill keeps a variety of board games at the bar for families to play. The Cooling Station serves ice cream, sorbets, yogurt and hotdogs. They also have a make your own stuffed animal party package for special occasions. The Bent Fork is an amazing collection of sweets and desserts. They specialize in gift baskets for holidays and other occasions, made the same day of shipping and guaranteed fresh.

Highwood Avenue has the Pastificio where Italian dishes are served. The Hoagie Hut on Bank Lane has been making cheese steak hoagies since 1966 and still serves them up today. Taco's El Norte on Washington is the place to go for Mexican food at a great price, and the Shrimp Walk Seafood Restaurant on Lake View Avenue offers Cajun and Creole seafood indoors or outdoors for its customers.

Besides the dozens of fantastic restaurants, Highwood has scheduled dates for some summer events. Highwood Festival Days run from July 19th through the 22nd. The Highwood Fine Arts Festival will take place on August 25th and 26th. And finally, the Harvest Days and Sidewalk Sale happens on September 29th and 30th.

Visit Highwood this summer and bring an appetite. You won't be disappointed.