Guidebook for Ashland
Arts & Culture
The most highly regarded Shakespeare festival in the country!
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Oregon Shakespeare Festival
15 South Pioneer StreetThe most highly regarded Shakespeare festival in the country!
Oregon Cabaret Theatre
241 Hargadine StYear-round productions.
Food Scene
Award-winning restaurant & wine bar. You can see it from our front porch!
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Winchester Inn
35 S 2nd StAward-winning restaurant & wine bar. You can see it from our front porch!
Ruby's
163 N Pioneer StBest breakfast burrito in town! Get the RBG!
During the summer it is fun to sit in this open-air restaurant, have a beer and watch the goings-on.
Water Street Cafe
10 Water StDuring the summer it is fun to sit in this open-air restaurant, have a beer and watch the goings-on.
Expensive, but maybe the best restaurant in Ashland.
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Umami Sushi & Asian Cuisine
62 E Main StExpensive, but maybe the best restaurant in Ashland.
Excellent high-end restaurant run by an industrious couple! Creative, delicious cuisine.
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Coquina
542 A StExcellent high-end restaurant run by an industrious couple! Creative, delicious cuisine.
A local brew pub with an extensive menu and nice outdoor seating. Good for kids. Beer is mediocre in our opinion, but has improved over the 6 years we have lived here.
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Standing Stone Brewing Company
101 Oak StA local brew pub with an extensive menu and nice outdoor seating. Good for kids. Beer is mediocre in our opinion, but has improved over the 6 years we have lived here.
One of two Caldera locations in Ashland. This location has a more extensive menu, views of the foothills and a better beer selection.
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Caldera Brewery & Restaurant
590 Clover LnOne of two Caldera locations in Ashland. This location has a more extensive menu, views of the foothills and a better beer selection.
Great little growler station with a great beer selection that changes almost daily. Grab an RBG burrito at Ruby's next door and enjoy a pint.
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Gils
175 N Pioneer StGreat little growler station with a great beer selection that changes almost daily. Grab an RBG burrito at Ruby's next door and enjoy a pint.
Authentic Mexican food at the back of the market. Oh so good!
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La Tapatia Mexican Restaurant
Authentic Mexican food at the back of the market. Oh so good!
This is a new spot in Ashland that we really like. Great coffee and food with outdoor seating. It is only several hundred yards from the rental!
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Hither Coffee And Goods
376 E Main StThis is a new spot in Ashland that we really like. Great coffee and food with outdoor seating. It is only several hundred yards from the rental!
Possibly the most popular breakfast spot in town. It is always busy, but for good reason.
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Morning Glory Cafe Permanently closed
1149 Siskiyou BlvdPossibly the most popular breakfast spot in town. It is always busy, but for good reason.
Ostras! Tapas and Bottle Shop
47 N Main StExcellent Tapas and creative cocktails.
Drinks & Nightlife
Great food and the best bartenders in town! You can't go wrong here.
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Liquid Assets
96 N Main StGreat food and the best bartenders in town! You can't go wrong here.
A beautiful winery in the foothills of Ashland with great views and excellent wine.
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Belle Fiore Estate & Winery
100 Belle Fiore LnA beautiful winery in the foothills of Ashland with great views and excellent wine.
Our favorite local winery. It is a bit of a drive, but it is beautiful and you will pass through historic Jacksonville.
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Cowhorn Vineyard & Garden
1665 Eastside RdOur favorite local winery. It is a bit of a drive, but it is beautiful and you will pass through historic Jacksonville.
Parks & Nature
Amazing large park. Great for walks, trail runs, picnics and has a great play area for kids
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Lithia Park
Winburn WayAmazing large park. Great for walks, trail runs, picnics and has a great play area for kids
Garfield Park
Great for kids! During the summer check out the free water play area of kids.
Great covered sandbox for kids. Great place for spotting dear, turtles, ducks and the occasional snake.
North Mountain Park Nature Center
620 N Mountain AveGreat covered sandbox for kids. Great place for spotting dear, turtles, ducks and the occasional snake.
Great little local ski resort with great hiking in the summer and views of Mt. Shasta.
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Όρος Ashland Ski Area
11 Mt Ashland Ski RdGreat little local ski resort with great hiking in the summer and views of Mt. Shasta.
Fun place to have a picnic and go for a swim. During the summer the waterslide is open!
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Emigrant Lake
Fun place to have a picnic and go for a swim. During the summer the waterslide is open!
Essentials
A little far away from down town, but this is our go-to grocery store with excellent produce, good prices and lots of local options.
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Ashland's Own Shop'n Kart
2268 Ashland StA little far away from down town, but this is our go-to grocery store with excellent produce, good prices and lots of local options.
Expensive, but centrally located grocery store with lots of local options. This is an Ashland staple and great people-watching spot. The deli is excellent! Have them make you a sandwich for a picnic in Lithia Park.
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Ashland Food Co-op
237 N 1st StExpensive, but centrally located grocery store with lots of local options. This is an Ashland staple and great people-watching spot. The deli is excellent! Have them make you a sandwich for a picnic in Lithia Park.
This is the closest grocery store and is within walking distance of the rental.
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Safeway
585 Siskiyou BlvdThis is the closest grocery store and is within walking distance of the rental.
Entertainment & Activities
Ever heard of an "Escape Room"? Sounds a bit sketchy, we know, but this is a REALLY fun activity for a small group. You have to solve puzzles to open secret compartments and doors to "escape" from the room. Well worth the time and cost. Schedule a session before going out to dinner!
Escape Ashland
509 Siskiyou BoulevardEver heard of an "Escape Room"? Sounds a bit sketchy, we know, but this is a REALLY fun activity for a small group. You have to solve puzzles to open secret compartments and doors to "escape" from the room. Well worth the time and cost. Schedule a session before going out to dinner!
Varsity Theatre
166 E Main StGreat little local movie theater. Very close to the house!
This is a great spot for kids! Lots of indoor educational and fun activities.
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ScienceWorks Hands-On Museum
1500 E Main StThis is a great spot for kids! Lots of indoor educational and fun activities.
Shopping
Ashland Liquor Store
40 Lithia WayAshland's local Liquor Store, with wine store located downstairs.