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A more easy-access segment of the Ice Age Trail starts 12 miles north of Medford on 13, at the wayside east of the highway. From there, hike east as far as you want, then back out by the same route.
The Pine Line trail runs north out of Medford for 26 miles on the abandoned bed of the Wisconsin Central Railway. It threads its way past forests and bogs, and through quiet little hamlets like Whittlesey and Chelsea. The gravel surface is suitable for mountain bikes, ATVs and horses in summer - snowmobiles in winter. Don't worry about traffic; it's generally lightly used.
This is a one-hour hike on a ridge above a lake, a half mile each way, mostly level except for some elevation change at the end. The trail follows the top of a sandy esker deposited by the last glacier, so it's a good hike when every other trail is muddy, and it would be hard to get lost on this trail. The trail is about 22 miles northwest of Medford, at Mondeaux Flowage. Get there from Medford by taking WIS-64 west 5 miles, then CTH-E north 14 miles, then FR-1563 east three miles. Then to find the trailhead from the dam, go west a couple hundred yards up the hill to the parking lot at the top of the ridge. The trailhead is across the road from the parking lot, marked as the Leopold Trail. This is a nice hike at any time, but on a clear fall day with bright leaves against blue water it can be glorious. Late in the day is also good, when you'll probably see wildlife swimming around the lake at the end of the trail.
Another charming short hike is the one-mile loop to Jerry Lake, an undeveloped small lake nestled in the forest. You can reach the trailhead from Medford by taking WIS-64 west 4 miles to CTH-E, then E north 5 miles to CTH-M, then M 7 miles west to Sailor Creek Road/FR-571, then one mile north to the sign for Jerry Lake on the west side of the road. For the shortest loop, follow the trail behind the sign west a couple hundred yards to the lake. Follow the trail to the left (SW) along the lake, then up over the ridge back out to the road. Then walk the road north back to your car. This hike can be extended by following the Ice Age Trail on the other side of the road, where you'll cross the Yellow River after a mile and then come out to CTH-M after another mile. That extension is not a loop; you'd backtrack to Sailor Creek Road.
Another section of the Ice Age Trail traverses this State Natural Area about 20 miles northwest of Medford. A good place to access is from Sailor Creek Road, just four miles north of the parking site described for Jerry Lake above. You should see a little "Ice Age Trail" sign along the road. If you reach the T with Lost Lake Road/FR-111, you missed the trail sign and should backtrack a mile on Sailor Creek Road. Once you find the trail, follow it east for the esker itself. The first quarter mile crosses a soggy bottom where the stream broke through the esker long ago, but then you get up on the esker and hiking should be dry. If you have two vehicles, you can park the other on Lake 19 Road/FR-108 for a nice three-mile thru-hike. The DNR webpage linked above describes plant and animal communities you'll see along the trail, and includes a rough map.