Easy to Start, Creative Side Hustles in the Driftless
Notice I said, “Easy to start,” but none of these are lazy gigs. Living in the Driftless offers beauty, space, and quiet, but it also brings a certain amount of practical difficulty. The same hills and distances that make this region feel open also separate people from stores, services, and one another. Many residents live on land that requires steady attention, and some houses stand empty for long stretches before filling again for a season.
In such a place, daily life takes planning. A trip into town is rarely for one purpose alone. Groceries, supplies, errands, and appointments are gathered together because the miles between them are real. What cannot be done that day often waits, sometimes longer than intended.
So small needs accumulate. A driveway left uncleared. A listing never updated. A house unopened after winter. Nothing large enough to justify formal help, yet enough to trouble the ease of living here.
Out of these small gaps, a quiet local economy appears. Those who live nearby and are able take on what distance has delayed. They clear, carry, check, repair, or bring what is needed. This is not hustle or enterprise in the usual sense. It is simply the exchange of usefulness within a scattered landscape, where proximity itself has value.
Thrift Reselling (Driftless Edition)
Near Lands’ End, the donation stream is unusually good. Estate cleanouts, retirees downsizing, and quality outdoor brands quietly flow into local thrift shops. People who know what to look for pull out wool, outerwear, vintage kitchenware, and cabin-style decor and resell online or locally.
Bargain Nook (Spring Green)
137 S Winsted St, Spring Green, WI
https://www.bargainnook.org
(608) 588-6325
This is one of the most consistent sources in the area.
Coffee-Shop Shelf or Micro Booth
Tiny towns don’t support full retail stores anymore. But shelves inside coffee shops or artisan spaces still work because people are already browsing while they wait. Locals and tourists both impulse-buy small home pieces when they’re relaxed and caffeinated.
They already sell artisan goods, which means customers expect to look around.
Estate Leftover Buying & Rural Flips
Rural estate sales often end with houses and barns still full. Families live far away or don’t want to sort decades of belongings. Locals sometimes buy remaining contents cheaply and resell tools, antiques, furniture, and kitchenware piece by piece.
You’ll see these sales around:
Spring Green
Mineral Point
Dodgeville
Richland Center
The supply is steady because land turnover is steady.
Rural Delivery & Errand Runs
Many Driftless residents live far from stores or can’t drive easily. A simple grocery or pharmacy run can save someone an hour of travel. Some locals quietly earn repeat income just running supplies into town and back.
Common anchor stores for runs:
Bender’s Foods (Muscoda)
122 W Nebraska St, Muscoda, WI
(608) 739-31125
Prem Meats & Catering (Spring Green)
1940 US-14, Spring Green, WI
https://www.premmeats.com
(608) 588-7892
Distance turns errands into services.
Cabin & Second-Home Checks
Seasonal homes are common across the Driftless. Many belong to families who live in Madison, across the line in Illinois, or down near Chicago. They come for long weekends, trout season, fall color. In between, the houses sit quiet through wind and weather.
Owners can’t easily check on a place after a heavy rain or a deep freeze. So someone local stops by once a month. They walk the perimeter, look for broken branches or forced doors, listen for a sump pump running too long. Before a visit, they might air out the rooms, turn on the heat, brush off the porch, restock paper goods and coffee. Small preparations that make a house feel ready instead of abandoned.
You’ll see these homes clustered along the Wisconsin River corridor, in the hills around Spring Green, along the ridges near Avoca, and through rural stretches of Sauk County and Iowa County.
Absentee ownership leaves space for steady, practical work. It’s not complicated. It asks for a truck, a good eye, and the habit of showing up. In a region shaped by distance and weather, that kind of presence has value.
Dump Runs & Donation Hauling
In many Driftless towns, households carry their own trash and recyclables to collection sites. For those without a truck, sufficient time, or the strength for repeated lifting, this ordinary task can become a burden. It is common, then, for someone nearby to haul a load to the dump or the thrift store on another’s behalf.
The work is plain and often unnoticed, yet nearly every household requires it at some point. What seems mundane proves widely shared, and usefulness lies simply in doing what must be done and carrying it a little farther down the road.
Avoca Area Collection Site
Avoca, WI (Iowa County)
https://www.iowacounty.org/recycling
If you live here, you already know how often this chore happens.
Furniture & Rustic Decor Flips
Rural Facebook Marketplace often holds more good furniture than local buyers can use. Solid wood tables, dressers, and cabinets pass from one household to another at low prices simply because supply is steady and demand nearby is small. Many pieces need little more than cleaning and care to be useful again.
When someone takes the time to restore and relist them, they often find buyers willing to travel from larger towns such as Madison or Dubuque, where such furniture is harder to find or costs more. In this way, what is plentiful here gains value through attention and distance, moving from one place of surplus to another of need.
Search hubs people use:
Spring Green
Dodgeville
Richland Center
Prairie du Chien
Older furniture holds surprising value once cleaned and staged.
Animal & Farm Check-Ins
Animals are common and services are sparse. When owners travel or work long hours, someone local feeding dogs, checking coops, or transporting animals to the vet becomes essential. It’s quiet, repeatable income built on trust.
Regional vets people already use:
Spring Green Animal Hospital
506 Rainbow Rd, Spring Green, WI
https://www.springgreenanimalhospital.com
(608) 588-7171
Animal logistics are harder in rural areas, so help is valued.
Snow Shoveling & Winter
Driftless winters are physical. Long driveways, drifting snow, older residents, and seasonal homeowners who arrive to buried entrances. Reliable snow clearing becomes essential very quickly.
This can include:
long driveway shoveling
walk clearing
entry access for deliveries
pre-arrival clearing for cabins
Winter repeats the same labor needs after every storm, which means repeat income for anyone dependable.
Christmas Lights & Seasonal Setup
Many rural homes are tall, steep, or set at angles that make a ladder feel uncertain. Old farmhouses rise higher than they look from the road, and newer homes often sit on hillsides where footing is uneven. Climbing onto a cold roof in November is work best left to someone steady and used to it.
Older residents still want a line of lights along the eaves or a wreath lit on the porch, but they no longer care to wrestle tangled cords in the wind. Second-home owners may not even be here when the season turns, yet they want the place to look tended when snow comes.
Hiring someone local to hang and remove seasonal lights is a matter of safety and trust. The work is careful and repeatable—measuring runs, fastening clips against the wind, setting timers, then taking it all down clean and dry after the holidays. It’s practical winter income built on being reliable and close by.
So locals quietly earn money putting up and taking down:
holiday lights
wreaths
garlands
porch decor
seasonal displays
This is short-window seasonal income with almost no competition in small towns.
Gravel Driveway Raking & Reset
Long gravel drives develop ruts, washouts, and potholes constantly. After snowmelt or heavy rain, they need leveling. Many homeowners don’t own equipment or can’t manage the labor.
Light rake-leveling and smoothing is a simple seasonal service.
This works because gravel never stays neat.
Getting the Word Out
Most of this work doesn’t come from advertising. It comes from being part of the place.
You tell a few people what you’re willing to do. Not in a selling way, just in the course of talk. That you’ve been keeping an eye on a cabin for a family out of town. That you stop in after storms. That you can open a place up before folks arrive. In small communities, that kind of sentence tends to travel on its own.
A handwritten card tacked to the grocery store board is often enough. A short note in the local online group can help too. Keep it simple; monthly checks, storm inspections, getting homes ready for visits. Name and number. Nothing more.
After that, the work speaks for itself. If you notice a loose shingle before it becomes a leak, if the heat is on and the walk is clear when the owners pull in after dark, they will tell someone. In rural counties, one good report along a ridge road can turn into three more calls by spring.
Reputation carries farther than any sign. Do the job carefully. Send word when you’ve been there. Let reliability and quality be what people remember.
The Driftless Side Hustle Pattern
None of this work depends on dense population or wide internet reach. It grows from rural facts that aren’t changing anytime soon: long distances between towns, aging neighbors who need a hand, second homes that sit empty half the year, estates that must be sorted, and stores that close earlier than folks expect.
Out here, extra income rarely looks like a startup or anything that spreads fast.
It looks like someone hauling a load to the dump in a borrowed trailer.
It looks like someone checking a cabin after a hard rain.
It looks like thrift finds cleaned up and set neatly on a shelf.
It looks like handmade mugs lined up beside a coffee counter in town.
It looks like groceries carried down a gravel road before dark.
Small, useful, human-scale work.
In places where services are sparse, usefulness carries its own weight. If you show up when you say you will, do the task carefully, and leave things a little steadier than you found them, there will be more to do. Around here, that is how side income grows, quietly, through need, trust, and the simple act of being nearby.