Ashland is a small, vibrant city that sits at the foothills of the Cascade Mountains in the Rogue Valley.
Ashland is a treasure with beautiful mountain scenery, stunning crater lakes, a rich cultural scene, award-winning wines, and a warm community.
The city caters to all kinds of local and international tourists, including nature lovers, art enthusiasts, the outdoorsy, or if you want a calm and relaxing vacation.
This article covers many ways to spend time and make lasting memories in Ashland, Oregon.
1. Attend Oregon Shakespeare Festival
The Oregon Shakespeare Festival is one of Ashland’s most popular events. It’s held every year, from February to October, with the Angus Bowmer, Thomas, and Allen Elizabethan theatres putting on spectacular shows.
From Shakespeare’s plays to other classic and contemporary performances, the festival offers something for everyone to enjoy.
Visitors are also treated to fun and free pre-show entertainment at the Green Show Courtyard and Stage, which features live music.
This festival promises to be the highlight of your visit to Ashland as the energy of thousands of theater-goers adds a contagious excitement.
Ashland hosts several other festivals that are worth your time, such as:
- The Independent Film Festival occurs in spring and is hosted in the Varsity Theatre, the Ashland Street Cinemas, and the Historic Ashland Armory. The 5-day film festival showcases documentaries, short films, and feature-length films.
- Ashland Culinary Festival aims to celebrate the region’s chefs, restaurants, winemakers, brewers, farmers, and chocolatiers. This 4-day festival occurs in November, attracting locals and tourists alike.
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2. Visit Lithia Park
We’d gone downtown Ashland when we noticed a beautiful leafy park surrounded by shops and cafes.
And immediately, we abandoned our downtown plans and got exploring Lithia Park. It’s set around the sparkling waters of Ashland Creek.
This is coupled with the incredible beauty of ornate fountains, lush green landscapes, beautiful gardens, duck ponds, and sycamore groves.
With several picnic spots, tennis courts, playgrounds, and miles-long hiking trails, visitors will always have things to do. And you know what? We didn’t pay a dime to get into the park!
3. Go Hiking
Ashland is a nature-lovers paradise. The best part is it has numerous hiking trails that will allow you to experience its vast wilderness.
The first trail is the 5-mile Lithia Park hillside trail just above Lithia Park. It offers stunning views of the city’s flora and fauna.
Hikers will also find a swimming hole, towering trees, a herd of deer, and a beautiful creek along the way.
Pacific Crest Trail is also quite famous and offers stunning scenery and landscapes. It spans 2,650 miles, with some secluded sections found near Ashland.
Be sure to reach the picturesque Cascade-Siskiyou National Monument, about a one-hour drive from Ashland.
Other popular hiking trails include:
- The Grizzly Peak
- The Hobart Bluff trail
- Acid Castle Rocks
- The White Rabbit Trail
- Oredson Todd Woods
- Alice in Wonderland trail
4. Take A Wine Tour
I love a glass of good wine! With dozens of vineyards and wineries, a wine tour is a must-do activity in Ashland.
There are many different types of wines to suit novice and fine wine connoisseurs alike.
Some of the best places to sample exquisite wines are:
- The Belle Fiore Estate and Winery
- Irvine & Roberts Vineyards
- Dana Campbell Vineyards
- Weisinger Family Winery
If you prefer beer, head to the Standing Stone Brewing Company or Caldera Brewing Company, which offers classic and seasonal beers.
5. Have Some Delicious Delicacies
Do you love comfort or fast food, or are you more upscale and looking for international cuisines?
Ashland has many great places to fill your tummy while making your taste buds happy.
Popular restaurants and eateries in this city include:
- The Greenleaf Restaurant: Located downtown, the restaurant serves fresh food for every meal.
- Peerless Restaurant and Bar: This upscale restaurant has delicious seasonal dishes, a lively atmosphere, and elegant garden seating.
- Alchemy Restaurant and Bar: This fine dining venue offers award-winning cuisine, craft cocktails, and exquisite wines in an elegant atmosphere.
- Larks Home Kitchen Cusine has the best comfort food in town
- Martolli’s Hand-Tossed Pizza: Enjoy a custom-made hand-tossed pizza with various wines, beers, and non-alcoholic drinks.
- The Oberon’s Restaurant & Bar features classic British dishes with the most aromatic entrees.
6. Water-Based Activities in Ashland, Oregon
The Rogue and Klamath rivers are great for water activities, including rafting, swimming, fishing, canoeing, kayaking, and boat tours.
The rushing rivers also offer stunning views of crystalline water, gorgeous landscapes, and lush forests.
7. Take a Trip to Emigrant Lake County Park
This large recreational area is about 5 miles outside Ashland.
It’s an excellent location for nature lovers, water sports enthusiasts, and sunbathers, as it has several picnic areas, a campground, water slides, and a snack bar.
Visitors can also engage in outdoor activities such as camping, bonfires, boating, kayaking, swimming, hiking, fishing, rock climbing, picnicking, and more.
8. Enjoy Various Performances And Food At The Oregon Cabaret Theatre
An excellent attraction for theatre fans is the Oregon Cabaret Theatre.
Various acts occur here by highly talented artists, including comedy shows, murder mysteries, musical performances, drag shows, and more.
In addition to the wonderful entertainment, guests can enjoy appetizers and a special menu accompanying each production.
9. Have Fun in Winter at Mount Ashland
Mount Ashland Ski Area is ideal for stargazing, weddings, reunions, and hiking in the summer. But have you considered visiting in winter to experience the sparkling snowcaps?
It’s one of the region’s best ski destinations, catering to novice and more experienced skiers. Visitors can rent equipment at a ski resort and on-site ski shop.
Mt. Ashland provides opportunities for other winter activities, including snowboarding, snowshoeing, mountain biking, sledding, and so on.
And with amazing views of different mountain ranges, well-groomed runs, and surrounding natural landscape, it’s a well-worth place to spend the day.
10. Visit the Schneider Museum of Art
Art lovers have a place to enjoy diverse, unique art pieces. The museum is open year-round and accessible to the public.
It showcases artwork from students and regional and national artists. And the best part is it has a rotating exhibition so you can see something new with each visit.
11. Relax At the Lithia Springs Resort
After a day of exploring the city and engaging in outdoor activities, you’ll need to rest.
We stayed at the Lithia Springs Resort, and our experience was extraordinary. The staff was friendly, and the rooms were clean and well-kept.
But that isn’t all! The resort has mineral springs that are perfect for unwinding after a long day of touring Ashland.
They also have a clean and big pool, Jacuzzi, lobby fires, and a seating area near the koi pond.
As you can see, Ashland features lasting natural beauty. From majestic mountain ranges to beautiful creeks, magical waterfalls, large and lovely parks, and crystalline lakes, there’s plenty to see in this region.
The favorable weather allows many outdoor recreational activities. Ashland is the perfect destination for adventurous, curious people and travelers looking for a calm and relaxing trip.
Be sure to reference the above activities to ensure your time is well spent creating unforgettable memories. We enjoyed our trip here and highly recommend you visit Ashland.
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