Labor Day Weekend, September 3-5, is quickly approaching. Here’s a suggested itinerary for those visiting Ashland, Oregon for the long holiday.

Saturday, September 3rd

Arrive in Ashland and shake off your driving legs with a nice walk through Lithia Park. Back in the plaza, sit down for a bite to eat at Greenleaf (located in the Plaza) immediately below a great British Pub known as the Black Sheep. Feel like a drink? Check out the Sheep and enjoy a great view of downtown Ashland. If dessert is what you are after walk down the plaza to Mix, a shop that features phenomenal ice creams and pastries. Each Saturday is the local grower’s market and it’s well worth checking out. Fresh veggies, fruit, and local meats can be found on Oak Street between Lithia Way and N. Main. Local artists set up booths along the creek on the backside of the Plaza area. Street musicians and entertainers are a common sight and the mood is festive and fun.

Sometime mid-afternoon you’ll want to check into your hotel and unload your bags. The Palm Motel of Ashland is located about half a mile from the heart of downtown and features cozy rooms and a wonderful pool. After checking in, head to the pool, grab a lounge chair and relax. For dinner, take a short walk to Omar’s, the famous restaurant and steakhouse only a few blocks away.

Sunday, September 4th

Whitewater Rafting with Indigo Creek Outfitters
Whitewater Rafting with Indigo Creek Outfitters

Start the day off with a phenomenal breakfast at Morning Glory, located one block away. Get the salmon scramble and a cup of coffee – it can’t be beat. Take a walk through the Southern Oregon University campus (across the street) and then trek into downtown Ashland. Check out art galleries and window shop through downtown. Ashland has lots of small businesses, each with their own style, and there’s something for everyone. For lunch, give Creekside Pizza a try.

From Creekside, walk down to Indigo Creek Outfitters‘ River Center (2 blocks away at 130 A Street) for an afternoon of whitewater rafting on the Rogue River. You’ll spend some time at their shop getting fitted with a lifejacket and then they’ll transport you to the Rogue River. Float 5.5 miles on Oregon’s most famous river. You’ll be back at their River Center by 5:30 and from there it’s an easy walk for a tasty beer and light dinner at The Playwright (also located on A Street).

Any visit to Ashland is not complete without seeing at least one of the performances by the Oregon Shakespeare Festival. Most evening plays start at 8:30. Make sure you get your tickets early because the shows are often sold-out the day of the performance. By the time the play is over you’ll be ready for a good night’s sleep at the Palm.

Monday, September 5th

Grab a breakfast burrito at Ruby’s Restaurant on North Pioneer Street before hitting the road back home. Their breakfast burritos are the best in town and will make the start of your drive home much more enjoyable.

Ashland, Oregon: Labor Day Weekend 2011

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