Having spent six glorious days in Portland, Maine (which is much longer than the average tourist ) I got a pretty good idea of all the funnest things to do while you're there. So in order for your experience to surpass mine (a tall order, I promise, but possible) I present to you your Portland checklist, in order: 1. Go before Columbus Day but after Labor Day. We went after Columbus day, and unfortunately many of the tours and museums shut down at that point. There is still stuff to do, but you might find yourself frustrated by the closed signs. On the other hand, the leaves are out after Columbus day, so that is definitely a consideration. Before Labor Day, well, you're just part of the masses of annoying tourists. 2. Rent a bike from Gorham Bike and Ski. It's $25 per day or $100 for a week, and worth every penny. Portland is definitely walkable, but you'll find the 1 1/2 mile from end to end much more enjoyable on a bike, promise. There's also a beautiful bike path that follows the waterfront. 3. Sign up for the Portland Foodie Tour. Portland is a foodie's dream, with 300 restaurants, well-known chefs, more coffee shops and breweries than your bladder can handle, and markets specializing in local foods. You'll want to get the lay of the land from an expert, so do this your first day. A guide will provide you will samples from some of the best stores and markets, as well as point out all the best restaurants at which to book your reservation. Bring a notepad and pen, you'll want to write everything down. 4. Visit the farmers market to stock up on snacks for your vacation. Cheeses, fruit, honey, even lotion can be found. If nothing else, the cute dogs and toddlers at the market will make you smile. 5. Take a Casco Bay boat tour to one or all of the islands. The scenery is quiet and beautiful, and makes for a great bike ride. I would suggest doing this before Columbus Day. If you come after it's not worth it as all the cafes, restaurants, and museums will be closed. 6. Look to see if any good bands are coming to town at the Portland Music Hall or State Theater. 7. Take a ride on the old steam train at the Narrow Gauge Railroad Co. and Museum. Do I need to explain why this is awesome? 8. Visit the Portland Museum of Art. It's a wonderful space with interesting exhibits, great sculpture and European art. 9. Make reservations for dinner every night at some of the hottest eateries like Street & Co., Bresca, Five Fifty-Five, Duckfat, Boda, The Salt Exchange, and many others. 10. Have a famous brunch at Bintliff's, Mercy's, Mims, Hot Suppa, and/or Front Room. 11. Get some Maine cheeses from the Public Market House. They give out samples and some of the cheese are the best in the nation, officially. 12. Walk around the Old Port, and pop in the kitchen store, vintage shops, ice cream shops, lobster roll shacks, and all the other locally owned businesses. 13. Take a free tour of the the Shipyard Brewery. The tour itself isn't so great, but you get to sample the beer, and the gift shop has some good stuff, including all the different varieties by the case. (Just in case you're having a microbrew rager later on after the concert.) 14. Get a sampler of beer at Gritty's. It's the oldest Brewpub in Portland and brews its excellent beers right in the basement. If you already did that on the foodie tour, get a sampler at Sebago. The vibe isn't as cool at their pub compared to Gritty's, but the beer is pretty tasty. 15. Pick up one of the many local newspapers and fill in the crosswords over a cup of coffee or tea from an independent coffee shop. (Don't you dare visit a Starbucks or Dunkin' Donuts while you're there.) 16. Visit a used book store (there are several) and peruse the titles. 17. Take a tour of the Victoria Mansion if you at all have an interest in architecture, history, trompe l'oeil painting, or just big-ass houses. 18. Get a ticket to a sporting event like an ice hockey game or a baseball game. Both the stadium and arena are right in town.