Itineraries for Everyone
Experience Ashland Year Round
Enjoy Ashland with these itinerary ideas...
Family Snow Day
Brothers Restaurant
Breakfast at Brothers — great menu for kids and adults alike brothersrestaurant.net
Table Mountain Snow Park
Head up to Table Mountain snow park for some sledding & warm up by the fire traveloregon.com
Hot Chocolate at Mix
Late afternoon warm up with hot chocolate & coffee from Mix — might as well grab a pastry too mixashland.com
Pizza Dinner
Everyone loves Pizza for Dinner - check out The Great American Pizza Company and be sure to try the dough-knots! greatamericanpizzacompany.com
Couples Getaway
Callahan’s Mountain Lodge
Come for the food and stay for the beauty in this winter retreat. Consider checking into Callahan’s Mountain Lodge for at least one night of your stay. callahanslodge.com
Brunch at Brickroom
Brunch at Brickroom-delicious food, cozy atmosphere and right downtown to make shopping after a no brainer. brickroomashland.com
Shop Jupiter Row
Stop into Jupiter Row for curated wears from makers around the world. jupiterrow.com
Wine Tour
Embark on a private wine tour for 2 with Bravo Outings - enjoy the wine and the majestic scenery and leave the driving to them. bravooutings.com
Dinner at Mas
A romantic dinner for two at Mas is the perfect way to wrap your day. Named as one of the 50 best restaurants in America by the New York Times and a nominee of the James Beard Foundation in 2023 and 2024. masashland.com
Arts & Culture
Ashland B&Bs
For a uniquely special experience consider staying in one of Ashland’s bed and breakfasts. stayashland.com
Schneider Museum of Art
With various exhibits throughout the year check out the Schneider Museum of Art on SOU’s campus. sma.sou.edu
Refuel at Sauce Fuel
your afternoon with delicious whole food from Sauce. saucewholefoodcafe.com
Studio + Gallery Tour
Spend the afternoon touring the various artist’s studios and galleries. ashlandgalleries.com
Show at the Oregon Cabaret
Entertainment and amazing food—grab dinner and a show at the Oregon Cabaret theater. oregoncabaret.com
Hit the Slopes
Grab coffee & a Treat at Noble Coffee
Start the morning with a cup of coffee, hot chocolate or a nice treat from a favorite Railroad District hot spot. noblecoffeeroasting.com
Ski Mt. Ashland
Head up the mountain early to get front row parking for the opening lifts at Mt. Ashland Ski Area! Lessons and rentals are available for kids or those who need a refresh! The lodge has fantastic hot chocolate and lunch for a mid-day break as well as a bar upstairs for those needing some colder drinks! Mtashland.com
Unwind at Callahan’s
Enjoy a good meal after a long day on the slope at Callahan’s Mountain Lodge where you can watch the snow fall and enjoy a cozy fireplace. callahanslodge.com