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Fall in Galena: A Weekend of Color, Cider & Stars

Our favorite fall days in Galena don’t usually involve a packed itinerary.

We might spend a morning biking through the hills, take a hike, wander around downtown Galena, or drive out to an orchard for apples and cider. Then we’re usually ready to head back to The Drey and enjoy the evening there.

That’s part of what we like about fall in Galena. There is plenty to explore, but you don’t have to fit it all into one day. Pick a few things that sound good, leave some room in between, and see where the weekend takes you.

Here are a few of the ways we like to experience fall around Galena.

Explore the Fall Landscape Around The Galena Territory

One of my favorite ways to experience a fall day is by bike riding around the Shenandoah Riding Center.

The area is hilly in spots, which makes it both a little challenging and fun to cruise around. The crisp air keeps you cool, and you can hear and smell the leaves as they shake in the trees and fall to the ground. At this time of year, the area is also quiet.

And then there are the horses.

I’ll hear them neighing in the distance and then stop to watch them graze in the fields for a while. I haven’t gone horseback riding at the center myself, but I’ve hiked along the horses while exploring the trails in The Galena Territory.

I feel pretty lucky to have these magnificent animals so close by.

Take in the Driftless Landscape at Horseshoe Mound

Horseshoe Mound is another favorite fall stop.

What I like about it is that you can enjoy the preserve in several different ways. You can park near the top and stay close to the level path and overlook, or you can head out on one of the trails and explore more of the preserve.

At the top is the Council Ring, a circular limestone gathering place with upright stones that mark solstice and equinox sunrises and sunsets. It has a Stonehenge feel, only this one is much closer to home.

The Council Ring is also a great place to stop and take in the views across the Driftless Area.

There are viewing scopes at the top that let you look out across the many hills surrounding Galena. I always enjoy spending a few minutes looking through them and taking in the landscape from a different perspective.

I like that Horseshoe Mound can be whatever kind of outing you want it to be—a quick stop for the view, a place to sit for a while, or a longer walk through the preserve.

Follow the Apple Harvest at Orchard Landing

One of the places I keep going back to is Orchard Landing.

It’s an unusual combination of an apple orchard and a grass airstrip, with horses nearby that you can feed apples. During apple season, I like going into the shop, sampling the different varieties and learning about them before choosing a bag to take home and use for pie.

And then there are the treats.

Apple cider donuts are a must. But if you’ve never tried an apple cider slushie, I highly recommend it.

I’ve also picked up hard cider to enjoy later, which makes a nice addition to a fall evening back at The Drey.

On one visit, I happened to catch a plane taking off from the airstrip!

It’s one of those unexpected things that makes exploring the area fun. You head out to an orchard for apples and end up watching a plane take off over the fall countryside.

Leave Some Time for Downtown Galena

We don’t usually try to fit downtown Galena into the same part of the day as everything else. That’s part of the pace we enjoy.

One morning, we might pick up coffee at Galena Roasters and an empanada at Galena Bakehouse, then walk across the bridge and sit on one of the benches in Grant Park for a while.

Sometimes that’s enough.

You can watch the day go by, take in the historic buildings and imagine what Galena must have looked like when those buildings were part of everyday life.

Then we’ll come back another evening.

I like stopping at Galena Cellars for a wine tasting and then wandering the shops on Main Street after some of the crowds have died down. If they have Apple Cask, I’ll bring a bottle home. It’s an apple wine with brandy spirits, and I think the flavor makes it almost a dessert on its own. They don’t always have it, which makes finding a bottle feel special.

End the Day Under the Stars at The Drey

After a day of wandering the hills and taking in the fresh air, I’m usually ready to head back to The Drey.

This is when I like to sit at the fire pit table and watch the stars.

Most of the time, I’m not doing much of anything. I’m just sitting there, looking up.

Then one of us will hear an owl hooting somewhere in the trees.

“Did you hear that?”

A little later, a dark shape might flash through the trees. A bat.

Then it’s quiet again.

The Galena Territory has been recognized by DarkSky International as a Dark Sky Friendly Development of Distinction for its efforts to protect the night sky from light pollution. On a clear night, you can see the stars without competing lights from the surrounding area. The Big Dipper is easy to find, and shooting stars are not unusual.

You don’t really have to try. You just have to look up.

I like that time of night because you feel connected to the trees and the sky. Being under the night sky makes you feel small and makes you dream.

And honestly, you hate to turn in for the night.

A Fall Weekend With Room to Wander

If you’re planning a fall getaway to Galena, you could spread these experiences across a weekend rather than trying to do them all at once.

Friday evening:
Arrive at The Drey, settle in and enjoy the fire pit.

Saturday morning:
Head into Galena for coffee and an empanada, then walk across the bridge and spend some time in Grant Park.

Saturday afternoon:
Choose one outdoor activity. Go for a bike ride, hike at Horseshoe Mound or explore the trails around The Galena Territory.

Saturday evening:
Have a wine tasting at Galena Cellars, wander Main Street as the evening crowds thin out, then head back to The Drey.

Sunday:
Explore Orchard Landing during apple season. Pick up apples, cider or an apple cider slushie and bring a little of fall home with you.

Or change it completely.

Maybe you spend the afternoon downtown. Maybe you skip the shopping and go for a long hike. Maybe you spend most of the day at The Drey.

There isn’t one right way to experience Galena.

Discover your own path. Create your own memories.

Come for Galena. Stay for the quiet.

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