Not every trip needs to be the kind of jet-setting journey that you’d put on a bucket list. Sometimes, the trips that cost just a drop in the bucket can be fun too — and all you have to do is hit the road to take them.

In the folded hills along the Illinois-Wisconsin state line, roads turn from striped highways to the plain asphalt of country byways, and the exteriors of businesses transform from a more modern look to a quaint callback to horse and buggy days. The scenery does the talking, and it does it quietly, as if to say “Take your time — there’s no hurry.” Ridges rise quickly just over the horizon, valleys open wide, and barns sit along country roads, reminders of the rural heritage that raised them.

Connect those dots on a map, and it makes for a unique road trip that takes people back in time. Step inside the grocery store in Scales Mound and the floor answers your footsteps. Around a bend sits a former rail stop that refused to fade when the trains did — and these days, music spills from the place instead of steam. A few turns later, across a state line one barely notices, another 19th-century storefront stands with its shoulders square to the road, where the shelves and bar are stocked with history that stretches back more than 175 years. Farther north, at a crossroads, a century-old tavern anchors the intersection like it always has, these days frequented by both locals and tourists who want to take a deep dive into the community’s past.

We’ve linked four unique and historical places in a 15-mile stretch, starting in a town that is the highest in Illinois, to a burg paying homage to the minerals mined for centuries. Check out these quaint stops and serene scenery that we’ve mapped out for you — or better yet, get in your car and turn the wheel.

Country House Grocery

501 Main St., Scales Mound

815-845-2316

Hours: 8 a.m. to 6 p.m. Monday through Saturday, 9 a.m. to noon Sunday

Online: Facebook, countryhousegrocery.com

Scales Mound (population 400) is unique among towns with fewer than 500 residents – it has its own grocery store.

The town has had a grocery store nearly every year since 1859, all located in a mid-1800s two-story white building now known as Country House Grocery. Customers walk the store’s four aisles on a vintage wood floor that still creaks and squeaks with each step, just like it did a century ago. The store carries grocery products, meat, produce and deli selections, as well as its own Country House Grocery apparel. Its brats are popular sellers, with original, jalapeno pepper jack, bacon cheddar and pineapple brown sugar varieties. Fresh baked buns include hard rolls, brat buns and Kaiser hamburger buns.

Melissa and Matt Dittmar have owned the store since 2021. It’s one of the historical centerpieces of Scales Mound, which was founded in 1853; 90 percent of the town is listed on the National Register of Historic Places.

Even with its history etched into the floorboards, the store’s real foundation, Melissa said, is the steady stream of regulars and returning tourists who keeps the lights on and the fabric of community stitched together.

“This is more about our community. If you don’t have your community to support you, you really don’t have anything,” Melissa said. “We serve a lot of local people, but we also serve a lot of tourists, and they’ve become our community, too, because they’ve come here so much.”

Council Hill Station

6527 North Hill Road, Galena

815-858-5276

Hours: noon to 5 p.m. Tuesday and Wednesday, noon to 6 p.m. Thursday and Sunday, noon to 7 p.m. Friday, noon to 9 p.m. Saturday

Online: Facebook

When the Illinois Central railroad laid out a track from Freeport to Galena in the early 1850s, it wound around the hilly terrain of Jo Daviess County known as the Driftless Region, an area untransformed by the glacial deposits of the most recent ice age more than 10,000 years ago. This necessitated the establishment of places in rural areas to serve as stations for passengers, mail and freight, and Council Hill Station was one of them. Along with a depot (now gone), the station also had a general store for many years. Long after its heyday had passed, owner Jamie Jones — who lives next door in one of the town’s two houses — resurrected the vintage-1854 general store and transformed it into a vintage-style bar and music venue.

Council Hill Station features live music every Friday, Saturday and Sunday afternoon and evening, from the folk tunes Jones has been singing for nearly 60 years to classic rock acts. Jones and his friends are regular musical acts. During the summer, music is played both outside the building and inside a barn at the back of it; performances are held inside the old general store in the winter. Musical performances have been a Council Hill staple since at least 1865, with the earliest known performance of the Council Hill Band.

“We have some great players,” Jones said about the revolving chorus of musicians who play there. “This is what draws people.”

Since taking over ownership 16 years ago, Jones has preserved the place’s history through stories, pictures and artifacts that adorn walls and shelves. The fire inside the building’s old stove furnace still crackles during the winter. Interested in more Council Hill history? Jones has put together a scrapbook of memories that visitors can read.

Jones’ longtime friend Gladys Ressler has performed at Council Hill throughout his time as owner, and she has helped him with the restoration of a limestone mill and a wooden hoop silo, both behind the store and dating to the early 1900s.

“The oldness and the laid back atmosphere makes you want to come back and hang out,” Ressler said.

On the other side of the railroad tracks is the old one-room Council Hill School, which has since been restored and is now a private home.

New Diggings General Store

2944 County Route I, New Diggings, Wisc. (Benton, Wisc. postal address)

608-965-3231

Hours: 3 to 10 p.m. Thursday and Friday, noon to 10 p.m. Saturday and Sunday

Online: Facebook, newdiggs.com

Lead mining was the primary industry in southwest Wisconsin from Native American days until about 75 years ago. New Diggings, founded in 1824, is a small settlement that pays tribute to those days.

Originally established in 1844, the New Diggings General Store has been a popular destination for a wide range of travelers for nearly 40 years, from motorcyclists to country tourists. The original store, which also housed a bar for its first 120 years, was located down the road from the current one and burned down in 1989. Later that year, Jamie Jones (who also owns the aforementioned Council Hill Station) restored a former hotel built in 1890 and transformed it into a bar, resurrecting the General Store name. It has been owned by Lou Uran and Kelli Kerrigan for the past 21 years, who have since added food, including burgers, pizzas, and smoked meat sandwich specials on the weekend.

A game room is at the back of the building, with a pinball machine, Foosball table and bristle archery target. An outdoor beer garden hosts occasional live music.

The wood exterior looks much like it used to around the turn of the 20th century, with vintage signs adorning walls both outside and inside. Even the bar room is a throwback to what the old store looked like a century ago, with wood floors and shelves filled with (now empty) cans and supplies shoppers would have found then. A small antique cash register, no longer in use, sits behind the bar and has a marble surface above the drawer. “Back in the day, they even counterfeited pennies and nickels,” Uran said. “They’d rub it on the marble and the lead on them would leave a mark.”

Tired and want to stay the night? That can be arranged: four upstairs sleeping rooms are available — two with single beds and two with doubles — each with their own bathroom.

“Meat Paddles” are held on Saturdays from October to April. In the raffle-type drawings, named for an old concept, people buy numbered paddles for a chance at matching a number on a spinning wheel to win cuts of meat. The event has people “rubbing elbows” there on these days, Uran said.

“We’re a destination,” Uran said. “We’re a town of 25 people. If you’re here, you’ve come from a distance. Our ‘locals’ are from a 30-mile radius.”

Leadmine Tavern

5389 County Route I, Lead Mine, Wisc. (Benton, Wisc. postal address)

608-759-6631

Hours: 3 to 11 p.m. Tuesday and Thursday, 1 p.m. to 2:30 a.m. Friday, 11 a.m. to 2:30 a.m. Saturday, 11 a.m. to 11 p.m. Sunday (may close earlier any day)

Online: Facebook, countryhousegrocery.com

Since the 1910s, the unincorporated community of Lead Mine (two words) has quenched thirsts at its crossroads tavern now known as the Leadmine (one word) Tavern. The exterior hasn’t changed much since its original days, giving it a classic look that is reminiscent of the days when leadminding was still a major industry in the area. Inside, the original bar counter still serves customers, having moved from the left side of the bar to the right about a decade ago. The tin ceiling, while painted over in beige, remains in place. The town’s oldest residents can recall the place once being Reilly’s Tavern, with an Old Milwaukee sign outside, where the current Leadmine sign is.

Today, the tavern, owned for 13 years by Dave Lacke, is best known for its “Leadmine Longies,” a selection of Long Island cocktail concoctions. They include, among others, a Marge Simpson of blue raspberry and lemonade (similar to the character’s appearance on The Simpsons); and a Purple Nurple, pitched on the menu as a drink that “hurt like hell in high school, [but] this will make you feel good.” Leadfest is the place’s primary event, with a long lineup of live music on the first Saturday in August.

In 2024, the tavern was voted as the No. 1 Dive Bar in the nation in the Dive Bar Road Trip online contest (go to divebarroadtrip.com for more information), and it finished as runner-up last year, leading to an increase of visitors from all over the nation, bartender Renee Geyer said.

“Everyone here is just friendly, kind, and we all get along no matter your age or where you’re from,” Geyer said. “We all just have a good time. From the Dive Bar contest to party buses, people come here from all over.”

Geyer remembers the year it won the dive bar contest, it had many visitors come from around the Quad Cities area, where people who frequented the defending champion, The Edge in Rapids City, wanted to see what made Leadmine special.

“Since we were in that, we’ve had so many Quad Cities people up here,” Geyer said. “They’ll come in bus-fulls and they’ve said, ‘We got to see who beat us.’”

The intersection where the tavern is located once had an alignment of the east-west state Route 11, with motorists needing to navigate a short, abrupt jog to get past the cross street. Route 11 has since been realigned south of Lead Mine. Next door to the tavern is the town’s former Odd Fellows Lodge and grocery store, now a private home but with its Odd Fellows identification stone visible near its roof.