The Run Down

Access to nature can sometimes feel inaccessible if you don't have a car. But for this guide, the Metra is all you need. You'll take the UP-N line to the North Shore where you'll walk through a field of wild flowers on a former military base turned nature preserve. The hike ends on a bluff overlooking Lake Michigan. After, you'll hop back on the Metra and take it one stop where you'll explore a charming downtown and grab a quick bite at a hot dog and sandwich shop. It ends at an old-school ice cream and candy shop for desert.

1. Hike @ Fort Sheridan Nature Preserve

Lunch @ Left Bank

Candy @ Sweets

1. Fort Sheridan Nature Preserve

Begin your trip on Metra’s UP-N line at one of these stops in the city (Downtown, Clybourn, Ravenswood, or Rogers Park). We started at the Clybourn station, near Bucktown. From here, you’re about 45 minutes to Fort Sheridan Nature Preserve.

On weekdays, the train comes about every hour. On the weekends, it comes about every two hours. Here’s the schedule for more details.

The train drops you off right outside the gates of Fort Sheridan and its 250-acre forest preserve.

Before entering the forest preserve, detour through the neighborhood and explore this architecturally unique residential community.

All the homes have a similar colonial-looking design made from the same yellow-hued bricks. The home designs look more like a historical neighborhood in Charleston, South Carolina, than Chicago.

As you get deeper into the neighborhood, it opens to a vast field with a massive tower overlooking it. Along this field are informational signs shedding light on this unique neighborhood.

Up until 1993, this whole area was an active military base with officers’ quarters, barracks, and other army administrative buildings. Thousands of soldiers called this place home. The fort saw its most significant activity during WWII when it was a training base for anti-aircraft artillery units and during the Cold War when Fort Sheridan maintained NIKE missile defense systems across the Midwest, including one at the Fort.

That all ended in 1993 when the base was closed. Buildings were refurbished and sold off as residences, some were donated to local organizations, and big swaths of land were turned over to the public and converted into a forest preserve. That’s where the journey takes you next.

There are nearly four miles of trail in the preserve. One trail branch leads you through a field of wildflowers and to a bluff overlooking Lake Michigan. Another trail branch follows a deep winding ravine created by ice glaciers millions of years ago that takes you down to a small beach.

During the hike, you’ll find preserved artifacts reminding visitors of the area’s military history. One of these preserved artifacts is an old anti-aircraft gun overlooking Lake Michigan.


They used to fire these over Lake Michigan for training purposes. That’s also why swimming and boating aren’t allowed off the coastline here — there is still the danger of potential unexplored artillery underwater. That’s a good enough reason to keep out.


2. Left Bank

Following your hike, hop back onto the Metra and journey one stop north to the city of Lake Forest. As the oldest among the North Shore communities, Lake Forest boasts sprawling estates, tree-canopied streets, and a quaint commercial district right where the train alights.

Market Square is the center of activity in Lake Forest. An artifact of early 20th-century urban planning, Market Square was one of the first planned shopping plazas built in the country. It feels like a small European town blending Tudor and Renaissance architecture and a pedestrian-friendly design.

Pedestrian arcades, walkways interspersed with shops and cafes allow you to weave in and around the plaza that spans multiple blocks.

For a casual post-hike meal, Left Bank is your place for all sorts of hot dog variations, sandwiches, and salads. Established in 1967, Left Bank filled the void of locally-owned, budget-friendly, family dining options—a contrast that stands out even today amidst the predominantly upscale eateries.

Here’s their menu to get a better sense of things.

We opted for the Polish hot dog and the intriguingly dubbed “not so sloppy joe.” This take on the classic comes brimming with cheese and childhood nostalgia. Its genius, however, is in the delivery: encapsulated in a pillowy brioche bun, ensuring every flavorful bite is captured, with nary a drop of sauce out of place.

3. Sweets

Finally, before heading back to the train, a few doors down is another longtime favorite in Lake Forest. Opened and family-run since 1982, Sweets is your classic small-town chocolate, cakes, and ice cream shop.

In the summer, a steady stream of kids park their bikes out front and enter the store, peering through the wooden counter’s glass casing where rows of chocolate pretzels, caramel apples, and store-made candies line the length of the store.

In the back, you can find about a dozen ice cream flavors from Cedar Crest Ice Cream, a Wisconsin-based ice cream maker that supplies ice cream to mom-and-pop parlors all over Illinois and Wisconsin. 

By the time you wrap up here, the next train home will soon arrive. But if you’re not in a rush, there are plenty of boutiques and small businesses worth exploring throughout Market Square, or head towards the lake and check out the massive estates that make up this historic town.