Highwood Hot Spots
Small in size, but big in character and rich in history, this is where the cool kids hang on on the North Shore! Here we go!
Eats!
28 Mile Vodka Distillery is fabulous for craft drinks, live music and delicious pizza. The rooftop makes this spot a true gem.
Longitude351 is fantastic South American cuisine! We love the food here and could probably drink the chimichurri sauce. There’s a lovely beer garden in the back for the warmer months.
Buffo’s has some of the best pizza on the North Shore and is super family-friendly. Service is fast so you can get and out in a jiff.
Clucker’s is a family dinner night staple in our house and, in our opinion, has the best roasted chicken on the North Shore.
Alex’s Washington Gardens is a super family spot owned and operated by two super North Shore families! The kids order the pizza, the adults order the fish – both are good!
Miramar Bistro is one of our favs and one of the few french restaurants in the area that has a fun vibe inside and ample outdoor seating in the warmer months.
In 2023 Noon O Kabab decided to open a second location, and we were thrilled they came to Highwood. This persian cuisine is rich in flavor and spice.
In 2024 Highwood welcomed Ami Jerusalem Street Food, which is just the chef’s kiss in terms of fresh and delicious Israeli/Mediterranean food done perfectly.
The North Shore isn’t known for its vibrant nightlife but if there ever was a place for it, Highwood is the destination. For bars and pubs that stay open past bedtime, head to Wooden Nickel, Teddy O’Brian’s and Toadstool!
If you’re looking for brunch 7 days a week, look no further than Sandy’s. The lines can be long on the weekends but the service is super quick with hot, solid breakfast fare.
And we can’t not mention Highwood staples like Maria’s for Italian pastries and home-cooked Italian food, well as Poeta’s for the sweetest family-owned Italian grocery store packed with frozen meals to take and bake.
Last but not least don’t forget the dessert! Head to Bent Fork for everything from cookies to bars, pies, cakes and party accessories, La Michoacana Bella for ice cream bars and Billy Bricks for pizza and ice cream!
And more….
Highwood isn’t well known for shopping, however, when you’re in town, we highly suggest you stop in at ABLAZE Design Group for the aesthetic home decor and delicious candles. This beautiful gift shop is home to a local and well-known design build service chock full of stellar reviews, and owned by a fabulous North Shore family.
Highwood’s Evening Gourmet Market is a must stop at least once over the summer. Typically this occurs on Wednesday nights and is host to kids’ activities and delicious food by local restaurants. It’s a great way to spend summer nights on the North Shore! Highwood also goes all out seasonally with festivals and events. Visit Celebrate Highwood and the Highwood Chamber to get a line up of all of the fabulous events from Pumpkin Fest to Garlic Fest and everything in between like bingo and lady’s night!
Don’t skip out on a play date at Giggles Play, one of the North Shore’s only indoor play facility. And if their sillies still aren’t out head to Everts Park for more running around this newly renovated park space complete with a splash area.
Highwood does not literally border Lake Michigan, but just north of Highland Park, and east of Highwood is the tiny town of Fort Sheridan. Fort Sheridan is so small, in fact, that many locals might be surprised to learn that it has its own zip code. Originally an Army post named after the Civil War cavalry general Philip Sheridan, the community has its beach access which is a popular hotspot for biking, trails for hiking and running, playgrounds, and forest preserves within a short walk. This gorgeous Lake County Forest Preserves land is a must for quick hikes.
We leave you with one more thing: We would be remiss if we didn’t celebrate Highwood ourselves by spreading the word about a fabulous, albeit short, documentary film that was just released in February of 2025 highlighting the rich culture and history of this amazing city. It’s well worth your 17 minutes. Watch here.
