Fifteen Reasons to Love Portland, Maine

Twenty years ago I lived in Portland, Maine. An undergraduate English major at the University of Southern Maine, I lived off campus, worked at shops and restaurants in the city's famous Old Port district, partied with friends in the pubs of that same district, biked and ran the miles of trails in and around the city, and studied in the many coffee shops that dot the colorful downtown. I even met my future husband in Portland. I knew I loved the laid-back yet surprisingly cosmopolitan lifestyle of this coastal city of 63,000 souls, but what I didn't realize as a young adult was just how unique this place truly is. I hadn't seen enough of the United States yet to know that vibrant downtowns and lovingly maintained historic districts are not the norm in many small-to-midsize American cities.

Then my boyfriend/future husband and I moved away. Over the next two decades, school and careers led us to a string of other cities and towns throughout the northeast and midwest. We liked most of the places we lived, and even loved a couple of them, but always in our hearts and minds, there was Portland with its brick Victorian mansions, stunning views of Casco Bay, and vibrant cultural scene. We knew we would eventually find our way back.

It took much longer than we'd hoped, but at last we moved back to Portland this year, and now I have the wonderful opportunity to live in a place that feels as comfortable as a favorite pair of well-worn L.L. Bean boots, but that also never fails to surprise me. Twenty years is a long time to be away; much has changed, so I now have the unique perspective of someone who knows the city well and who also has the fresh eyes of a tourist discovering sights and hidden treasures for the first time. With that perspective, I thought I'd share just a few of the reasons that I'm happy to call this city my home.

First, here's a short geography lesson to acquaint you with the city's layout. The center of Portland is situated on a peninsula. The two-mile long peninsula has two hills, one at each end, with a dip in the center. One of the hills is the Eastern Prom; the other is the Western Prom. Between them is downtown Portland. One long thoroughfare, Congress Street, runs like a spine from one prom to the other. While the city limits actually extend inland from here, most of the city's attractions and cultural life can be found on the peninsula. This fact, combined with a low crime rate, makes Portland a highly walkable city, especially in the spring, summer, and fall. Portland's location on Casco Bay provides residents and visitors with year-round access to beaches and islands.

1. The Portland Farmers' Market: We are lucky--very lucky. Our markets run year round with a host of local farmers and a very hungry and happy public turning out every week. In the spring, summer, and fall, the markets take place three times a week: at Monument Square in the heart of downtown on Mondays and Wednesdays, and in beautiful Deering Oaks Park on Saturdays. I buy all my fresh veggies and fruit at the markets in the summer and fall, plus there's gorgeous local honey, meat, handmade herbal soaps and remedies, and much more. And if that weren't enough, we have a Winter Market, too, which takes place on Saturdays at the Irish Heritage Center on State Street. Travel & Leisure named the Portland, Maine, Farmers' Market one of the Top 10 markets in the country.
2. Portland Trails: Part of the mission of Portland Trails is to create 50 miles of multi-use trails throughout the Greater Portland region. They are well on their way with more than 30 miles of trails to date. I have walked, run, and biked many of these trails, covering terrain that varies from fields to forests, from marshland to beaches, and from rugged coastline to urban jogging trails. You can click here for a map of the thirty trails, many of which link to one another. Many of these trails offer truly breathtaking views of Casco Bay.
3. Free Friday Nights at the Portland Museum of Art: We have a beautiful, world-class museum, housing works by American artists Winslow Homer, Andrew Wyeth, John Singer Sargent, Marsden Hartley, Louise Nevelson, and many more. The museum is also home to a large collection of works by European artists, including Pablo Picasso, Mary Cassat, and Edgar Degas, among others. In all, the collection includes more than 17,000 pieces--and on Friday nights between 5:00 and 9:00 it is free to see them! My husband and I sometimes make a date to grab a slice of Otto Pizza ($3 a slice for INCREDIBLE pizza) and eat it outside the museum while we people-watch. Then we go explore a gallery or two at the museum. We wrap up the night by buying tickets to see a great film at the museum's theatre. It's a cheap date, but a fabulous one!
4. First Friday Art Walks: Just as the name suggests, on the first Friday night of every month, the downtown arts district turns into one giant gallery opening. Remember when I mentioned above that Congress Street runs like a spine down the middle of the peninsula? Well, dotted along that spine are several fantastic galleries that throw open their doors for First Fridays. There's music in the streets, demonstrations, and a general party atmosphere. The Maine College of Art is right in the middle of the mix, making the whole place feel vibrant. I can't recommend this fun event enough, plus you can stop over at the Art Museum for their free Friday while you're at it!
5. Munjoy Hill and the Eastern Prom: At the far eastern end of Congress Street you'll find the neighborhood called Munjoy Hill. For decades, this was a dicey part of town. But today, enterprising business owners have taken advantage of low rents, great architecture, and the neighborhood's close proximity to the Old Port. Galleries, funky shops, and artist studios abound, as do hip coffee shops, bakeries, and restaurants. Stately Victorian homes, saltbox cottages, and early 20th-century apartment buildings are being lovingly renovated. While still affordable, the East Side of Portland is definitely coming up in the world. If you plan to go there, wear a good pair of shoes and climb the hill on foot. You'll want to stop in many shops, take a peek at the gorgeous cemetery, and maybe even climb up to the top of the Portland Observatory, the country's last remaining maritime signal tower. At the top of the hill, Congress street continues, dipping down towards the Eastern Prom. Every trip to Portland should include a walk along the Prom. Boasting some of the most breathtaking views of Casco Bay in the whole city, it is a great place for a picnic, with the ocean spread out before you and grand old Victorian homes behind you. There's even a small beach, East End Beach, and you can hop onto the East End walking trail from here.
6. The West End and the Western Prom: At the opposite end of the peninsula, high up on Bramhall Hill, lies the elegant West End, Portland's most beautifully preserved Victorian neighborhood. About a mile from the hustle and bustle of the Old Port, the West End's tree-lined streets offer many rewards to lovers of architecture--or anyone who dreams of living in a fine old brick or brownstone home. I recommend parking the car and wandering. There are several blocks to explore, with a stroll along the Western Prom a must. Here you will find impressive mansions and a lovely view of the Fore River. John Calvin Stevens, an important and innovative architect of the late 19th and early 20th centuries, designed several homes in the West End, many of which still stand as fine examples of Shingle Style and Colonial Revival architecture.
7. Pro Sports: Portland has three minor league sports teams. For basketball, we've got The Maine Red Claws, a Boston Celtics development team; for hockey, there's the Portland Pirates, an AHL affiliate of the Buffalo Sabres; and, last but definitely not least, we have Sea Dogs baseball. The Sea Dogs are a Double-A affiliate of the Boston Red Sox, and Hadlock Field, where they play, is a sight to behold on a warm summer night, complete with a 37-foot tall replica of Fenway's Green Monster, a picnic area, and a crowd of more than 7,000 fans. Catching a Sea Dogs game ranks among my all-time favorite family nights out.
8. The Old Port: This district is probably the number one reason most tourists visit Portland. It is the cobblestones-bricks-old-world-charm part of Portland in the historic streets and alleys that line the working waterfront of this old city. But what locals love about the Old Port is that it is real . Sure, it has the trinkety souvenir shops and fried seafood restaurants, but it also has local artists' boutiques, funky clothing and housewares shops, vintage stores, and just about anything else you need. The locals shop here. And we eat and drink here--a lot. Walk down Exchange Street and Fore Street; definitely take a stroll down the tiny alley that is Wharf Street, and don't forget some of the smaller, hidden streets. You'll find a dizzying array of pubs and restaurants, including some of the best in the country. See number 15 for more about that. What most of us love best about the Old Port, though, is the ambience. When I was a college student I worked in the Old Port, and I loved the bustle, the tiny parks, the grand architecture, and the people watching. There are very few chains in the Old Port. This isn't Disney World. It's a real, working neighborhood that just happens to be loaded with charm and the smell of salt air.
9. Coffee Houses: I could write all day about the coffeehouses in Portland. I won't, but I will tell you that no matter where you are on the peninsula, you are ALWAYS near a cafe. Some are better than others, and some are truly fantastic, but in most neighborhoods you will be able to find a great latte or espresso. My favorites are Coffee By Design and Bard for great coffee, Crooked Mile for good lunches and great atmosphere, and Arabica for their Maple Soy Lattes and great atmosphere. But these are just the tip of the proverbial iceberg. Come taste test for yourself.
10. Music and Theatre Venues: Whether you're itching to hear a local band at a pub, a popular indie band at one of the many music halls, or a major national act at the Cumberland County Civic Center, you can nearly always find great music in Portland. I recently saw Lyle Lovett and John Hiatt at The State Theatre, a beautifully restored theatre in the heart of the Arts District. Actually, most of the larger live music venues are on Congress Street in the Arts District, including the gorgeous Merrill Auditorium at Portland's City Hall, home of the Portland Symphony Orchestra. And if it's theatre you're craving, we have the Portland Stage Company, mounting seven shows a season to an annual audience of over 50,000 people. There are several smaller stages and troupes in and around the city as well.
11. Vintage Shops: Whether it's clothing, housewares, or books you're looking for, you will find plenty of second-hand shops in Portland. One of my favorite clothing stores is Find, a hip little shop on the border between the Old Port and the Arts District with an ever-changing array of vintage and contemporary merchandise. Up on Munjoy Hill, there are funky second-hand shops for exploring as well as a great used books store, Carlson & Turner. Heading along Congress Street towards the West End, the Arts District is home to several unique shops, including one of Portland's oldest and most popular vintage clothing stores, Material Objects, and just across from the Art Museum, Yes Books continues its long tradition of supplying Portland's many avid readers with a large and eclectic selection of used and rare books. No survey of Portland's scene would be complete without mentioning Mad World, the funky, fanciful, and wicked cool shop on Commercial Street featuring new, repurposed, and up-cycled green designs in clothing and housewares by owner Meredith Alex and other artists.
12. Architecture: One of the distinctive characteristics of Portland is its late 19th-century feel. This is due largely to a major fire in 1866 that destroyed many buildings on the peninsula. This then led to a major rebuilding of the city, particularly in the West End, but there are fine examples of Victorian architecture throughout Portland. An online visit to Greater Portland Landmarks will provide you with downloadable maps and information about tours, including self-guided walking tours through some of the city's most remarkable neighborhoods. You will notice as you walk through downtown Portland that most businesses and public buildings--and many private homes--are constructed of bricks. The few buildings built from other materials stand out against the bricks. One example is the Custom House, which was built with New Hampshire granite just after the Great Fire. Its blend of Renaissance Revival and Second Empire styles makes it a commanding and distinctive structure along the Portland waterfront. Even if you're just in Portland for the food and shopping, you will be charmed by its architecture and small scale. There are no skyscrapers in Portland, but plenty of fascinating buildings and public parks to enjoy.
13. Ferry Rides to the Islands: The islands of Casco Bay offer a special glimpse into life on the coast of Maine. I lived on one of these islands myself for four months, so I know firsthand the unique experience of island living. Never have I felt so in tune with the tides, sunrise, sunset, and the subtle, day-to-day changes in the seasons as I did living on a Casco Bay island. I've also never felt so warmly welcomed into a community. Neighbors wave as they pass you on the road, strangers strike up conversations at the post office that lead to dinner invitations and friendships. If you visit Portland, plan to take a ride out to Peaks, the island closest to the mainland. There you can rent a bike and ride all the way around the island, which takes less than half an hour. Lined with rugosa roses, wave-beaten rocks, and New England cottages, Seashore Avenue boasts one of the most beautiful stretches of ocean scenery you'll find anywhere. Back in the village, stop for lunch at The Cockeyed Gull, followed by an ice cream. Or pick up a coffee at the cafe to enjoy on your fifteen-minute ride back to Portland's Old Port.
14. Portland Head Light (and all the local lighthouses): A short drive (or bike ride) from the center of the city will take you to Cape Elizabeth, a suburb of Portland whose tree-lined streets are lined with elegant homes and mansions. The drive itself is lovely, but what makes Cape Elizabeth truly special is that it is the home of Portland Head Light, arguably the most photographed and painted lighthouse in the world. Portland Head Light has been a beacon in Casco Bay since 1791. Visit the museum at the lighthouse and then have a picnic on the adjacent grounds of Fort Williams Park. Be sure to bring your camera--or your paintbrush and paper! As you explore, you will soon understand why painters like Edward Hopper and poets like Henry Wadsworth Longfellow loved this lighthouse so much.
15. Food: I saved the best for last. Okay, so technically, I'm writing about food twice since I included the Farmers' Market as number one on this list, but Portland's restaurants and food festivals deserve a category of their own. This is one serious food city. The home of about 230 restaurants, Portland was named the "Foodiest Small Town in North America" by Bon Apetit in 2009. It was also selected as one of three finalists for "Delicious Destination of the Year" in 2007 by the Food Network. While Portland is obviously a great place to find fresh, local seafood, there is so much more to discover and taste here. For lovers of fine cuisine, there are restaurants with James Beard Award-winning and nominated chefs, including Hugo's, Fore Street, and Bresca--along with several other remarkable destinations, including one of my favorites, The Salt Exchange. To find delicious food and a warm atmosphere without spending your whole paycheck, look no further than neighborhood bistros like The Front Room, The Blue Spoon, and Local 188. Then there's pizza. Sigh. Portland has some of the best pies I've ever tasted, including the thin-crust wonders at Otto and Flatbread, both of which have a great family atmosphere, as well as the miracle that is the Sicilian Slab at Micucci's Market. And don't forget sandwiches. Silly's serves them up in a funky, friendly atmosphere; the Great Lost Bear offers burgers that many locals swear are the best they've ever tasted plus 69 beer taps to satisfy any thirsty traveller; and Amato's is the home of the Italian, Portland's own take on the sub sandwich. Portland also has more fantastic breakfast spots than I can count on two hands, so I'll save that for another hub. The same goes for ethnic restaurants--I've got much to say about those, too! And speaking of ethnic food, it's a good idea to include a festival in any visit to Portland. Two of my favorites are the Greek Festival in June and the St. Peter's Italian Festival in August. Seriously, if you come to Portland for nothing else, come for the food. You'll leave full, and maybe a little amazed by the variety and quality of the food this small city has to offer.

If these fifteen reasons haven't shown you why, then I don't know what could. Portland is just the sort of city where you feel welcome once you step over the threshold of your favorite pub, coffeehouse, or diner. It's a popular travel destination that doesn't feel overrun by tourists--yet. Dozens of cruise ships now visit Portland Harbor every summer, so the word is definitely out. If you want to visit, but would like to avoid the Old Port crowds, I recommend the fall for the foliage, the area harvest festivals, and beautiful weather. Whenever you come, I think you'll love it, too.