Ashland Oregon Trip In The Winter

Ashland Oregon Trip In The Winter

I’ve been going to Oregon for the past 30 years and as I booked my December flight tickets, I realized I have never been in the winter season. I am cold-adverse and the thought of cold blustery rain made me cringe, but we were going to visit family for the Holidays – time to suck it up.

Braced for less-than-ideal weather, I had lots of warm layers and umbrellas ready to go at a moment’s notice. Worried there would be very little to do outside, I also packed several books. Spoiler Alert – My books remained packed for the entire trip!

Although it did rain on an off, the weather was honestly not a deterrent. The storms were brief and we were treated to numerous rainbows (even double rainbows!) as the sun came out.

downtown ashland oregon during the holidays with lights

Downtown Ashland

I initially thought we would walk the historic downtown Ashland and be done in an hour, but to my surprise, we could have spent all day there. As we were there for the Holidays, the town was lit up in festive white Christmas lights and decor. The shops are unique, fun, and interesting and I ended up buying a lot more than I intended. Some of my favorite stops:

Ashland Book ExchangeGreat bookstore with new and used books. Take your previously read book in great condition to this store and trade it in for store credit.

Bloomsbury Books New books for sale, but there is a cozy coffee/wine shop upstairs. Great vibe! I wish I had time to plop down with a good book, coffee, and pastry – but again, I had no time!

Paddingtong store in ashland oregon

Paddington Family of Stores This retail group owns a few shops on the main drag and each one deserves a visit! The large Paddington Station shop is two stories and is chock full of fun and useful home decor and kitchen items.

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There’s no shortage of coffee shops, boba and foodie restaurant options. We had a large family dinner at Osteria La Briccola  – This restaurant is located upstairs and has an intimate vibe that lends to great conversation. We had outstanding food and service – specializing in Northern Italian cuisine and handmade pasta.

Cioppino from La Briccola in Ashland Oregon

Several of us ordered the cioppino and it was outstanding; chock full of delicious seafood and unlimited bread to dip in the broth!

Southwest of downtown, leafy Lithia Park surrounds Ashland Creek and features trails, duck ponds, and a rose garden. To the northeast, North Mountain Park has a nature center and themed gardens, like the butterfly and herb gardens. At the ScienceWorks Hands-On Museum, kids can build and experiment in the Da Vinci’s Garage space. 


Ashland, Oregon is known for its world-famous Oregon Shakespeare Festival.  and other theatre productions. We were fortunate to get tickets to a fun holiday show at the Oregon Cabaret. Just sitting inside this intimate theater is a treat as we had tables reserved for our group up in the balcony section. While we didn’t have dinner there, we did order drinks and yummy desserts. Its uniquely inviting ambiance and consistently high-quality productions have earned OCT a nationwide reputation for excellence that keeps its 140 seats full, six shows a week all year round. The theater is Check their upcoming schedule here

balcony view from the Oregon Cabaret Theater

If you have some more time to explore the area, I recommend a quick jaunt to Jacksonville and Medford.


Jacksonville is a designated National Historic Landmark District, with over 80 buildings on the National Register of Historic Places. Take a walk down Main Street and admire the well-preserved Victorian-era architecture.  The Jacksonville Museum of Art & History and the Jacksonville Cemetery are both great places to learn about the town’s gold rush history. There are lots of cute shops here, great dining, and some very interesting antique shops that invoke days gone by.

old town jacksonville oregon building on corner

We dined at the Bella Union Restaurant. Despite the chilly weather, they had ample heaters on their large outdoor patio that kept us snuggly, and they also had indoor dining. We had salads with their house-smoked salmon. So delicious! I’m still thinking about it! The pizzas coming out to other guests looked delicious.


The Rogue Valley is home to many award-winning wineries. Spend a day visiting some of the wineries in the area and sampling their wines. We made a quick stop to Edenvale Winery (known for sitting on their wines WAY over the industry average before release).

Edenvale Winery in Medford Oregon

This location is my favorite because of the historical Voorhies House and Carriage House tasting room. This is an idyllic place to sip wine in any type of weather! Click here to look at the Oregon Wine Trail to make a game plan. I hope to have time in the future to make a Rogue Valley Wine tasting tour trip.


Harry & David  – Did you know Medford is the home base for Harry & David, the popular national retail and online store? The Rogue Valley used to be planted with farms full of fruit trees to supply Harry & David. Although some fruit is now sourced out to other growing areas, you can still take a tour at their processing facility. The main flagship shop is still our favorite. We always stop to load up on pepper jellies and Moose Munch. If you go after a major holiday, you can save big on discounted holiday sets.

Rogue Creamery

An artisan cheese company, with people dedicated to service, sustainability, and the art and tradition of making the world’s finest handmade cheese. Most famously, Rogue Creamery is known for its Rogue River Blue, which was crowned World Champion Cheese at the 2019/20 World Cheese Awards. This achievement made them the first American cheesemaker to claim the top international honor. The blue cheeses here are by no means cheap, but if you’re a fan of GOOD cheese, this is the place to go. Also, make sure to grab a bag of garlic cheese curds! Yum!

Several airlines fly into Medford, Oregon, so it’s easier to get there than you think!

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