Above:Great Highwood Pumpkin Festival Photo: Denys Bucksten/Chicago Tribune
Don’t be fooled by Highwood’s size. This blink-and-you’ll-miss-it town may occupy less than a square mile, but it has a fascinating history, a lively restaurant scene, and some of the quirkiest events in the area: Garlic Fest, Inferno Fest (celebrating scorching foods), and Redhead Days, a gathering of gingers. Highwood is also home to Fort Sheridan, established by the army in 1889 when North Shore denizens were convinced the violence of Chicago’s Haymarket Riot would spread to their environs. The revolution never came, and the military base was eventually shut down. But even without it, Highwood remains a vibrant island of affordability north of the city.
1. Everts Park
The adorable little park (awww, there’s even a gazebo!) hosts the town’s evening market in summer and its many peculiar annual events.
2. Fort Sheridan
This 600-acre area was once a military training facility and missile service center. Now it’s the site of luxurious homes and the headquarters of Midwest Young Artists Conservatory, a renowned music program.
3. Highwood Bocce Courts
Opera singer and bocce fanatic Luciano Pavarotti played here during several visits to Chicago. No wonder: It’s one of the world’s top facilities.
4. St. James Catholic Church
Designed by noted Chicago architect Andreas Brisch, this elegant colonial-style structure features two large stained glass windows rescued from the 1912 building that previously housed the church.
5. The Art of Beer
Pick an ale from the dozens of craft beers at this bar and killer brew shop and imbibe while hanging out on the patio.
The owner routinely travels to Poland, Italy, and Spain, bringing an international vibe to the jewelry and clothing (think basics with an edge) at this charming boutique
7. Novedades Tanya
This funky all-purpose shop is the place to be if you want industrial work boots, children’s books in Spanish, or just a Dora the Explorer backpack.
8. Poeta’s Italian Food Market
Housemade Italian beef, frozen eggplant parmigiana like Grandma used to make, and balls of pizza dough—in other words, a classic Italian deli.
Get some French country flair with a fastidiously distressed table or some lush new blooms for your yard at this home and garden emporium.
Eat & Drink
10. Bent Fork Bakery
This two-room bakery—responsible for Tony Bennett’s 90th birthday cake—makes delish treats (did someone say homemade Ho Hos?) on one side and sells charming vintage goods (tea sets, cake stands) on the other.
11. Curry Hut
They take their bread so seriously at this beloved Indian and Nepalese spot that they have two ovens—one dedicated to their heavenly naan, roti, and paratha, and the other for everything else.
The rustic Italian decor makes it cozy; the pillowy gnocchi with braised lamb makes it a must-visit.
13. Froggy’s Restaurant
How has this French resto stayed popular since 1980? Could be the whimsical decor (upside-down umbrellas hang from the ceiling, local artwork on the walls). More likely, it’s the award-winning fare, like the grilled beef medallions with blue cheese cream sauce.
14. Maria’s Bakery
Sometimes you just get a hankering for a perfectly made cannoli. That’s when you drive to this homey bakery and restaurant for the Italian treat.
Look closer at this French bistro and you’ll find a subtle Cuban flair, including pressed sandwiches and zingy mojitos (served at the cool zinc bar).
October 6 to 8:The Great Highwood Pumpkin Festival celebrates all things Halloween, including hayrides, a hay maze, and even an effort to get into Guinness World Records for the largest display of lit jack-o’-lanterns.
October 7:This is no ordinary 5K—it’s a dress-up-as-a-superhero 5K to benefit the Make-A-Wish Foundation.
October 14:Local faves Dave Weld and the Imperial Flames bring their classic tavern blues to the Toadstool Pub.
October 26:Ditch the kids for a spooktacular (sorry) time—unlimited food and drink for 50 bucks!—at the Goblins Ball costume party at 210 Restaurant & Live Music Lounge.
Did You Know?
In the early 1900s, boisterous army personnel packed Highwood’s many taverns, leading President Theodore Roosevelt to call it the “toughest town in America.”