Merry Mileage: 3 Illinois Main Streets Voted Among the Country’s Most ‘Drive-Worthy’ Christmas Shopping Destinations.

Merry Mileage: 3 Illinois Main Streets Voted Among the Country’s Most ‘Drive-Worthy’ Christmas Shopping Destinations.

• Survey of 3,004 shoppers.
• Christmas shoppers are prepared to travel furthest to main streets in Woodstock, followed by Princeton + Geneva.
• 77% would drive to a town purely for the Christmas atmosphere.

Across America, certain towns transform into picture-perfect holiday shopping destinations – the kind of Main Streets lined with independent boutiques, twinkling lights, and storefronts that feel far more magical than the nearest convenient mall. But with Christmas crowds growing and travel habits shifting, how far are people really willing to drive for that nostalgic, small-town shopping experience? CashforCars.com commissioned a survey of 3,004 shoppers to find out, asking them how many miles they would drive to reach their favorite festive shopping street. 

The Top 10 Most “Drive-Worthy” Christmas Shopping Streets:

#1. Market Square, Portsmouth, New Hampshire — 6 hours
Market Square doesn’t just do Christmas — it transforms to it. Think 18th-century brick buildings and antique lampposts glowing like they were designed by Charles Dickens’ lighting department, and independent shops perfectly curated for gifting. Shoppers from across New England happily make a day of it (and half the night), treating the trip as a festive tradition rather than an errand. It’s the rare shopping district that feels like a holiday card you can walk through.

#2. Main Street, Hanover, New Hampshire — 5 hours 34 minutes
Hanover’s Main Street has that special blend of New England coziness and Ivy League sparkle — a place where bookstores spill warm light onto the sidewalk and cafés hum with students escaping the cold. Visitors say it feels like stepping into a winter novel: every corner is lined with artisanal gifts, glowing windows, and a kind of understated charm that rewards anyone willing to make the long drive up I-89.

#3. Broadway, Fargo, North Dakota — 5 hours
Broadway in Fargo is one of the Midwest’s most unexpectedly festive stretches. When December hits, the street transforms into a lively corridor of indie shops, creative wintry window displays, and bright lights that cut beautifully through the cold. People drive hours through wide-open prairie just to soak up that “city-energy-meets-small-town-heart” atmosphere Fargo pulls off better than almost anywhere.

#4. Spring Street, Eureka Springs, Arkansas — 4 hours 44 minutes
Spring Street is the beating heart of Eureka Springs, twisting up the hillside like a Victorian ribbon. At Christmastime, the entire town goes all-in — wreaths on balconies, elaborate window art, twinkling lights reflecting off the old limestone buildings. Shoppers say the trip feels less like a drive and more like time travel: three hours in the car, and suddenly you’re in a turn-of-the-century Christmas village that hasn’t lost an ounce of its charm.

#5. Main Street, Bar Harbor, Maine — 4 hours 40 minutes
Main Street in Bar Harbor turns into a coastal Christmas postcard, complete with evergreens, maritime touches, and storefronts that smell faintly of cinnamon and sea air. The snowy views of Frenchman Bay don’t hurt either. People make the trek for gifts you can only get in Maine — hand-thrown pottery, local jams, hand-knit everything — and for the peaceful, unhurried pace that gives the whole outing a restorative, winter-break feel.

#6. Main Street, Medora, North Dakota — 4 hours 39 minutes
Medora’s Main Street captures a kind of Western-frontier Christmas you didn’t know you needed until you arrived. Rustic wooden storefronts, big-sky views, and quiet streets wrapped in warm light make the whole place feel like a holiday film set with a cowboy twist. Visitors say the long drive is part of the appeal — the further they get from city noise, the more magical the final destination feels.

#7. Oklahoma Avenue, Guthrie, Oklahoma — 4 hours 36 minutes
Oklahoma Avenue leans fully into its Victorian roots during December. The historic brick buildings look tailor-made for wreaths and garlands, and holiday events spill into the streets. It’s a town where Christmas isn’t just “celebrated” — it’s performed. People come for the architecture, stay for the festive theatrics, and leave with the sort of gifts you tell friends you “found in the most surprising little shop.”

#8. Main Street, Blue Ridge, Georgia — 4 hours 24 minutes
Nestled in the mountains, Blue Ridge’s Main Street transforms into a high-altitude holiday escape. Locals decorate every inch of downtown; windows sparkle, lights trace the rooftops, and shops feel as warm as the fireplaces inside them. Visitors describe it as “the South’s coziest Christmas village,” and its mix of cabin-country charm and boutique shopping makes the four-hour drive feel more like a prelude than a chore.

#9. Central Avenue, Nebraska City, Nebraska — 4 hours 20 minutes
Central Avenue captures the kind of slow, thoughtful Christmas many people feel nostalgic for — family-run stores, and a pace that refuses to rush you. It’s a place where you can wander for hours without hearing a single mall jingle. Regional visitors say they go for the serenity as much as the shopping, and for the rare feeling that the holidays can still be simple.

#10. Dock Square, Kennebunkport, Maine — 4 hours 19 minutes
Dock Square is already picturesque, but Christmas pushes it into “storybook seaside town” territory. Every building glitters, the harbor turns into a backdrop of twinkling reflections, and holiday events give the whole area an unmistakable sense of occasion. Shoppers come for the boutiques — sure — but what really draws them in is that ineffable coastal magic that makes Kennebunkport feel like America’s unofficial Christmas capital.

Three Illinois main streets also earned spots among the country’s most travel-worthy Christmas shopping destinations:

#15. Woodstock Square, Woodstock — 4 hours
Woodstock Square transforms into a classic Midwestern Christmas scene, complete with twinkling lights and inviting local stores. Shoppers drive in for its nostalgic holiday atmosphere and charming boutiques.

#35. Main Street, Princeton — 3 hours 36 minutes
Main Street in Princeton offers a friendly small-town holiday experience, with decorated storefronts and plenty of local shops to explore. People travel in for its welcoming Christmas spirit and easy, festive stroll.

#59. Third Street, Geneva — 3 hours 16 minutes
Third Street shines during the holidays with beautifully lit trees, specialty boutiques, and elegant window displays. Visitors come from miles around for its upscale yet cozy Christmas shopping scene.

Infographic

After seeing just how far Americans were willing to drive for a Christmas-card Main Street, the CashforCars.com decided to dig deeper — not just where people go, but why. This is what they found:

What matters most when choosing a festive shopping town?

• Overall holiday atmosphere (lights, music, decorations): 26%
• Independent/local shops: 21%
• Food and drink options: 25%
• Special holiday events (parades, markets, tree lightings): 14%
• Avoiding big-box malls: 14%

Moreover, a quarter of Illinoisans admit that a town’s snacks and drinks are just as important as its shops – proof that gingerbread lattes and mulled wine still have a powerful pull.

What discourages people the most?

• Traffic/parking headaches: 15%
• High prices: 25%
• Large crowds: 21%
• Distance: 14%
• Bad weather: 24%

How Far Will Illinoisans Go for Holiday Charm?
Even with the above frustrations… Would people drive to a different town purely for the atmosphere?

• 77% say yes. Turns out, Americans will absolutely travel for vibe alone.

Which would they choose?

• A magical Christmas town, even if it’s farther: 68%
• A convenient but charm-free mall: 32%

Two-thirds of shoppers are willing to trade convenience for magic — a promising sign for small-town Main Streets everywhere.

Loyalty runs deep…

• 37% visit the same festive town every year
• 77% say Christmas shopping simply feels “better” in a small-town setting

What Motivates These Holiday Pilgrimages?
When asked why they hit the road each December, respondents said:

• Cute shops: 30%
• Instagrammable decorations: 6%
• Food & drink: 21%
• The “movie set” feeling: 12%
• Family tradition: 31%

Family rituals and independent shops clearly power most of the mileage – but there’s still a small, devoted group chasing the perfect festive photo.

“What really stood out is how far people are willing to travel for a sense of Christmas nostalgia. These towns aren’t just shopping destinations – they’re emotional landmarks”, says a CashforCars.com spokesperson. “People want that blend of lights, music, history, and community you simply can’t get at a big-box mall. If anything, it shows that Christmas shopping still belongs to small-town Main Streets.”