Things to Do on a Rainy Day in Ashland: An Insider’s Guide
Slow down and explore local art, cafés, and cozy hideaways. Visit Lithia Park after the rain, catch a show, or sip wine by the fire – all within minutes of Parkside Acoustic B&B.
It’s taken me some time to acclimate to life below the 45th parallel – it doesn’t rain nearly as much here in Ashland as it does up north, and I miss it sometimes. So when the clouds settle low over the Siskiyous and the scent of petrichor rises up from the dust, I am here for it.
With the rain, Ashland changes tempo. Locals still take their daily walks, and visitors still weave in and out of downtown shops, but conversations move inside, and people linger longer at the cafés.
Rain here isn’t a reason to cancel your plans – it’s just an invitation to slow down and see the town in a softer, more intimate way.
I was reminded of that recently, walking through Lithia Park during an early autumn rain. The Japanese Garden is only about a two-minute walk from Parkside Acoustic, and it’s a peaceful place to wander this time of year, so I go there frequently. In October, the Japanese maples and other deciduous trees are at their peak, and when it rains, the colors become luminous.
I had a small, lovely moment by the koi pond. As I walked out onto the bridge, the koi darted toward me, breaking the surface in greeting – I was delighted! It was only as they made a quick u-turn to swim back from whence they came that I realized the why. Apparently, they had mistaken raindrops on the water for me throwing food (a big no-no!) until they came closer. (If fish can look dejected, they did.)
For me, the moment was a gentle reminder that even on a rainy day, Ashland offers joy and wonder for those willing to slow down and notice.
Here are a few favorite ways to spend a drizzly day in Ashland – all within easy reach of Parkside Acoustic Bed & Breakfast!
Ashland’s creative energy doesn’t hibernate when the weather turns wet – it simply moves indoors. Start at the Schneider Museum of Art on the SOU campus. It’s quiet and free, with thoughtfully curated exhibits featuring Pacific Northwest artists alongside national names.
For families looking for something more hands-on, ScienceWorks Hands-On Museum offers colorful, interactive exhibits that spark curiosity in both kids and adults.
The Ashland Artisan Emporium is a treasure trove for art lovers and antiquers alike. You never know what you’ll find among its aisles of vintage goods, vinyl records, rocks and minerals, jewelry, art, and clothing. (This is where we found our Silvertone cabinet!)
And of course, there’s the Japanese Garden – a calming, centering place to visit in any weather.
Insider tip: If your visit falls on a First Friday Art Walk, bundle up, grab an umbrella, and join the locals. Live music spills into the streets, and you can hop from one gallery to the next between rain showers.
Rainy evenings are made for red velvet seats and stage lights. While the Oregon Shakespeare Festival slows in winter, the Oregon Cabaret Theatre keeps the spirit alive with cabaret-style musicals, comedies, and dinner shows inside a beautifully restored church. Whether you’re enjoying a pre-show dinner or slipping in for drinks and dessert at intermission, the dining pairs beautifully with the Cabaret’s productions.
Or, if you’re in the mood for something quieter, settle into a plush seat at the Varsity Theatre downtown for a warm bag of popcorn and an afternoon matinee.
One of the great joys of a rainy day in Ashland is that it gives you permission to linger. Start at Bloomsbury Coffee House, tucked above the bookstore – order a latte, pick a window seat, and watch the umbrellas go by.
For excellent coffee and pastries, Case Coffee, Remix, and Mix Bakeshop are all good bets. La Baguette Music Café has live music every Wednesday and Saturday morning from 10:30 to 12:30.
When you’re ready for something heartier, Morning Glory serves breakfast from 8:00am to 1:00pm Thursday through Monday in a brightly painted old house near the university.
For a cozy lunch or dinner, you can’t beat the housemade thin crust at Creekside Pizza. (They have an excellent gluten-free crust, too.)
For more dining ideas, check out Where to Eat in Ashland.
I have spent a lot of time in small town libraries over the years (hat’s off to Sheridan, Wyoming!), so believe me when I say, the Ashland Library is everything you hope for in a small-town library. Housed in a beautiful historic building, its updated interior makes the collections easy to browse, and staff are friendly and always ready to help.
If you prefer to own your books (🙋🏻♀️), Bloomsbury Books (below the coffeehouse) is a longtime independent bookstore specializing in contemporary fiction, children’s books, nonfiction, and local authors – plus, of course, a large Shakespeare and theater section.
Paddington Station, Prize, and Treehouse Books are just steps apart – each filled with amazing and unique gifts, books, and curiosities that make time vanish.
Love a mystery? October brings Ashland’s annual Mystery Festival, where authors, readers, and sleuths gather for readings, signings, and intrigue all over town.
For a more interactive kind of storytelling, Escape Ashland offers two live-action escape rooms – The Scottish Play and The Ramblin’ Rogue Saloon – both within walking distance of downtown theaters. They’re great fun for couples, friends, or families, especially when you’re dodging rain showers.
Ashland sits at the southern edge of Oregon’s wine country, where winter tastings feel intimate and unhurried. Weisinger Family Winery and Dana Campbell Vineyards both have cozy tasting rooms with fireplaces and wide windows framing the misty hills.
If you’re in the mood for chocolate, be sure to pay a visit to Branson’s Chocolates here in town. Super nice people, excellent chocolate selection. (They make our chocolate covered graham crackers!)
If your timing is right, February brings the Ashland Chocolate Festival – a town-wide ode to cocoa that pairs beautifully with a gray weekend getaway.
If the drizzle turns steady, take it as your cue to unwind. Waterstone Spa downtown offers massages and facials with organic ingredients, while Chozu Bath & Tea Gardens invites you to soak in warm pools surrounded by bamboo and rain. Few things feel more luxurious than being immersed in hot water while the sky quietly drops its own.
For a full-service experience, The Blue Giraffe Spa combines massage, med-spa, and salon services under one roof.
Lithia Park & Japanese Garden
Open year-round, free admission.
The Japanese Garden is especially beautiful after a light rain – bring your camera and a quiet heart.
Oregon Cabaret Theatre
Location: 241 Hargadine St.
What to Expect: Intimate cabaret-style shows with table seating and dining options.
Tip: Book early if you want dinner service; desserts at intermission are a local favorite.
Bloomsbury Coffee House & Books
Location: 290 E Main St.
Why Go: This local favorite is excellent for quiet mornings and people-watching.
Dana Campbell Vineyards
Location: 1320 North Mountain Avenue
Vibe: Cozy tasting room with a fireplace and sweeping valley views.
Open: Daily, 1pm–6pm.
Read our Local Spotlight for more.
Escape Ashland
Location: Two downtown sites – The Scottish Play (166 E Main St.) and The Ramblin’ Rogue Saloon (509 Siskiyou Blvd.)
Good to Know: Games run 60 minutes; book online to guarantee your slot.
Chozu Bath & Tea Gardens
Location: 832 A Street
What to Expect: Japanese-style soaking pools, tea room, and massage services in a serene bamboo courtyard.
Reservations Recommended
After a day of wandering, there’s nothing better than returning to warmth. Back at Parkside Acoustic Bed & Breakfast, the rhythm of the rain plays out on the roof. Guests can settle into the music room with a cup of tea and a guitar, or a curl up by the fire with a good book.
Sure, rain might shuffle your plans a little, but in Ashland, it rarely spoils the fun. The whole town seems to take a breath – galleries feel cozier, coffee shops hum a little softer, and the air smells like earth and cedar.
Pack an umbrella if you must (Portlanders, you’re exempt), and come ready to explore. A rainy day here has its own kind of magic.
Leave a Reply