Walk to the end of that loading pier you see there.

(The bakery and the Black Cat, that is.)

I would hit up Prentice park also if you like parks.  

The El Dorado or something like that has pretty solid Mexican food.  It's to the right on Highway 2 when you come in.  Come to think of it, Prentice park and and El Dorado (or whatever) are right by each other. 

I would hit one of the three main Pizza places: Hugo's, Pizza Pub, and Frankie's (all started by the same family, I think.)

I always hit the artesian well at the beach that is by Prentice Park and El Dorado's (Pretty sure that's the place) and stock up on the best water in the area.  Is it Meyer's beach? Can't remember.  

Depends on if you are talking Ashland or Ashland Area.  Houghtoun Falls was just opened to the public and it is a very pretty but quick hike.  It is on the outskirts of Washburn on the far side of the town.  

I will see if I can't think of anything else to come up with and will post it here if I do.

There's also one of the finest disc golf complexes in the country just outside town.

I have always said that the best thing about Ashland is the view of Washburn across the bay.  I would definitely head over to Washburn (just north on HWY 13) and check out what that little town has to offer.  Coco's bakery rocks for breakfast, lunch and fine bakery (chocolate hedgehogs and cinnamon rolls that will change your life), Chequamegon Books: the best BAR NONE bookstore in the tri-state northern region, Karlyn's Gallery for locally created art and pottery, Memorial and West End parks on either side of town directly on the big lake, Houghton Falls trail north of town, the walking trail along the lake, DaLou's Bistro for wood fired pizza and kick ass gelato, Patsy's for a beer or 3 (you are in Wisconsin!), Leino's gas station for unleaded or gluten free snack products, North Coast Coffee for a shot of espresso....I could go on.  

But, if you are going to limit yourself to Ashland, the Whole Wheat Triangle area of Chapple Ave. that houses the Black Cat Coffeehouse, Ashland Baking Co. and the Chequamegon Food Co-op is definitely the place to start.  

Enjoy!

Ashland is a great town.  It's Bayfield w/o the snob appeal.  The BlackCat is a must as is the Ashland Baking Co.  The bakery has divine products that are different than any in our area.  The Bistro is good I hear as is the Deepwater grill on "west" Main St.  It's the home of the South Shore Brewery and its food is good.

5. Alas, the days of freely walking out on the Oredock have passed, but you can still get fairly close to it by walking the shoreline trails beside it (and you can peek through a hole in the big metal barricade to see what you're missing). 

6. The Northern Great Lakes Visitor Center (on the western edge of town, just west of the Hwy 2/Hwy 13 intersection) has some cool displays about the history of the area (geological and cultural), plus some walking trails and a lot of interpretive events throughout each month. (http://www.northerngreatlakescenter.org/)

7. All the good things people have written about the Ashland Baking Company are true! If you get there early enough in the summer, you might be lucky enough to snag one of their fresh fruit danishes, which are DELICIOUS.