Known for lobster, miles of coastline, and landscapes that have inspired artists for centuries, Portland may be our coziest Trail to Tavern® city yet. Once the capital of Maine and still the largest city in the state, this industrial town has turned into a true foodie destination with about 200 restaurants and more than 20 breweries (and that number grows each year). Pair that with more than 70 miles of urban trails, and you’ve got a full weekend ahead. But with so many options, how do you make the most out of three days in Portland? Even just walking, eating, and drinking your way across the Forest City would be considered a major accomplishment. But we’re going to get you off the peninsula, too, and pack as much as possible into the three days you have here.

Day One

The Eastern Promenade is easily accessible from downtown, and is a popular spot for locals. murphman61

Start your first day at sunrise (trust us, it’s worth it!) on Munjoy Hill. The spot is located in the Eastern Promenade, and you’ll have the best vantage point for breathtaking views of Casco Bay, Fort Gorges out on Hog Island Ledge, and other nearby islands. The "Eastern Prom" offers a 2.1-mile paved and stone trail along the water that is perfect for running or biking, and also connects to the 3.6-mile Back Cove Loop if you want to add in more mileage. After finishing your run back at the Eastern Prom, take a dip in the ocean at East End Beach, or bring your kayak or canoe and launch right off the beach or the boat ramp. (You can also rent a kayak or stand-up paddle board at the promenade.) Paddle around the bay, or go under Tukey’s Bridge to the calm Back Cove. By now, everyone else will probably be awake, so make your way down the hill for coffee at Coffee by Design on India Street with some of the friendly locals. Committed to the environment, their partners in South America, and the community, the micro roaster offers up perfectly brewed flavored coffees (and single origin black coffee, too!) and tasty pastries like handmade donuts from The Holy Donut. After a little breakfast, head over to the Casco Bay Lines’ terminal for a 20-minute ferry ride out to the biggest nearby island, Peaks Island. The first boat leaves at 5:45 am, and then every hour after that until the last boat at 11:30 pm. The schedule may vary, so check the ferry website. You’ll need fuel for your upcoming adventure, so stock your backpack full of bread, cheese, meat, and delicious spreads from Rosemont Market or Standard Baking Co. before boarding the boat. Once you do get out to the island, beeline it to Brad’s Island Bike Rentals & Repairs. Making your way around the island via pedal power is the best way to take in all in. You’ll find birds to watch, beaches to explore (check out the back shore), and Battery Steele, a fortification from World War Two. The Umbrella Cover Museum is a quirky little place featuring (you guessed it!) umbrella covers, and with a motto of "Celebrate the Mundane!" Of course, paddling is almost always an option when you’re on an island, and the Maine Island Kayak Company is the place for rentals or guided tours. There are half-day and full-day options that are suitable for beginners or those with a little more experience, and your guide will take you out to "secret" areas that are tough to find on your own (think a lighthouse, a lagoon with starfish and lobsters, and more). If you have self-survival skills, they will rent you a kayak in the warmer months of July and August, but the tours are worth checking out. It’s 100% okay to bring a boat beer for the ride back, so stop by Hannigan’s Island Market (about a three-minute walk from the ferry) for a wide selection of local brews. Sometimes you can even snag a seasonal beer that is sold out on the mainland! Once you get back on the mainland, head over towards the Back Cove to the family-owned Rising Tide Brewing Company. Making small-batch beers with an "aim to create well-balanced beers that are inspired by old world traditions but with modern twists," they offer tours and tastings throughout the week. You’ll also find a food truck there most days. If you didn’t find something to snack on at Rising Tide, wrap up your day with dinner at The Thirsty Pig, serving up house-made sausages and local beer. With options ranging from a pork sausage with Thai chili sauce to a Lithuanian Kielbasa, this place is a must stop for good beer and food. You can even get vegan chili and vegan hot dogs for the non-meat eaters in your crew. Where to Stay Portland has several chain hotels, but for an authentic experience, look into a bed and breakfast. There are several in town, each with their own character. The Danforth Inn is just south of downtown, near the Casco Bridge, and is housed in the renovated Old Port Mansion. A few blocks away, the Inn at Park Spring is a little smaller with just five rooms in an old brick house dating back to 1835. A third option is the Inn at St. John, which is a little closer to a hotel than a B&B. With 39 rooms, it’s the oldest continuously operating Victorian inn (built in 1897).

Day Two

Founded in 1995, Allagash Brewing Company focuses on Belgian beers. Allagash Brewing Company

After filling your first day around and on the water, we’re heading inland for day two. Before leaving the peninsula, though, fuel up at Tandem Coffee Roasters on Congress Street in the West End. The cafe is known for espresso and drip coffee, as well as muffins and mouth-watering cinnamon rolls. A 30-minute drive from Tandem will get you to Pownal’s Bradbury Mountain State Park. The park is home to nine trails ranging from flat and easy to steep with sharp turns, all converging at Bradbury’s summit, with views of Casco Bay and Portland’s skyline on a clear day. The trails are short (the longest is 1.5 miles), but it’s easy to link them up for more mileage. All of them are open to foot traffic, but a few are open to mountain biking and horseback riding, so be aware of who might be coming up behind you. After working up an appetite, drive just a half-mile back to Pownal Center to Edna and Lucy’s, a locally-owned cafe serving up a menu of quick bites like sandwiches, wraps, salads, and soups. The options change daily, but make sure that you save room for dessert—they have some of the best old-fashioned German donuts in the state! Pownal is very rural compared to Portland, but it’s a mere five miles from downtown Freeport. This former sleepy village is now a busy retail outlet town, so Main Street offers all kinds of shopping for clothing, jewelry, and outdoor apparel. Turn off Main onto Bow Street and see what’s new in the local Toad&Co store while you’re in town. After leaving downtown Freeport, point your GPS south towards Maine Beer Company on your way out of town. While Maine Beer Co. is all about their beer, they’re also a brewer with a conscience, committed to reducing, reusing, and recycling. Knowing that you’re supporting a company who cares about the environment might just make their Lunch IPA or Maine Peeper taste even better than they already do! If you want to grab one more drink on your way back to Portland, stop by Allagash Brewing Company right off the Maine Turnpike. Allagash focuses on Belgian-inspired beers and is known for their flagship Belgian white. They offer 10 beers year-round, plus some limited editions, and a few brewed with spontaneous fermentation, a traditional Belgian method of cooling hot, unfermented wort overnight with outside air. They offer free tours and tastings daily (by reservation), just get there before they close at 6 pm! Right across the street from Allagash is Foundation Brewing Company, with a core line of more traditional beers (an American IPA, a brown ale, etc.), but also unique flavors like the cherry Magnus and an apricot sour ale. Once you get back to town, meander over to the other side of the city for pad thai or drunken noodles at Boda, then watch the sun set over the Western Promenade.

Day Three

There’s plenty to discover when hiking the trails in Portland. Terry Cockburn

Spend your last day in Maine hitting the trails in Portland. Portland Trails, a nonprofit urban land trust, maintains the 70 miles devoted to hiking, walking, and mountain biking throughout Greater Portland. Visit the Presumpscot River Preserve, a 48-acre public preserve, for a tough 2.5-mile route through a ravine and wooded areas to the Presumpscot River. Another solid option is taking Andrews Avenue out to Mackworth Island, a legislated bird sanctuary. The 1.25-mile loop on Mackworth is relatively flat and follows the perimeter of the island. There are fantastic views of Casco Bay, and also a few side trails that lead down the steep slopes to the beach. What better way to wrap up a Trail to Tavern weekend than with a trip on the environmentally friendly Maine Brew Bus? Rarely does a month pass without word that yet another brewery has opened, so the easiest way to hit some of the best spots is to hop aboard the bus and leave everything in the capable hands of your tour director and bus driver. The company offers several different tour options, from the Southern Crawl through southern Portland to Breaking Brews (exploring the newest breweries) to the Curling and Brew Tour that throws in a trip to the Portland Ice Arena for some friendly competition before heading to two local breweries. Before you leave town, we highly recommend taking your time to enjoy a family-style meal at Empire Chinese Kitchen in the heart of the city’s art district. Known for their dim sum (tasty Chinese dumplings filled with things like mushrooms, pork, and lobster), their extensive menu offers something for everyone, including vegetarians and vegans. Right about now, you’ll begin to wonder how the last three days have flown by—and there’s still so much to see! The good news is that the friendly locals will welcome you back to the Portland of the East whenever you’re ready, but you’ll be planning your next trip in no time. Originally written by RootsRated for Toad&Co. Featured image provided by Allagash Brewing Company