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Portland is the largest city in the state of Maine, set on a peninsula extending into Casco Bay. It was named after the English Isle of Portland. The first European settler was Christopher Levett, an English naval captain who was granted 6000 acres of land by King James I in 1623. Maine was part of the Commonwealth of Massachusetts until 1820 when it voted to secede to become a separate state. On March 15, 1820 it was admitted to the Union as the 23rd state. Today, the Old Port district is the town's historic heart, with cobblestone streets, flickering gas lamps and restored redbrick warehouses filled with shops, restaurants and bars. Portland has become one of the hippest, most vibrant small cities in America. With its excellent museums and galleries, abundant green space, and both a food culture and a brewing scene worthy of a town many times its size, Portland is sure to please.

Start your journey by wandering the Old Port district. This southeastern side of the city is listed on the National Register of Historic Places. At first glance you will see a quaint seacoast town with a working waterfront representing Maine’s roots in a robust fishing community. You will also find a vibrant community of small business owners whose stores, galleries and restaurants represent the true heart of what it means to be a Mainer - pride, hard work and fine craftsmanship. Be sure to stop in to some of the many boutiques lining the streets. Cool as a Moose on Fore Street is the place for fun Maine apparel and souvenirs. Up the road is Old Port Candy Co where you can satisfy your sweet tooth with a dozen flavors of fudge and an array of chocolates ranging from peanut butter to sea salt and bacon. If sniffing the salty ocean air puts you in the mood for some seafood, your go to destination is the Harbor Fish Market. A local landmark since the 1800s, this iconic market on Custom House Wharf is the number one destination for locals and tourists alike in search of lobster in Maine, and the freshest seafood in New England. If you want to experience what it's like to be a Maine lobsterman, hop aboard one of the Lucky Catch Cruises at Commercial Street. You will take in the sights of beautiful Casco Bay while hauling up traps from the bottom of the ocean and learning about one of Maine’s favorite crustaceans - the lobstah.

Next, make your way to the Portland Museum of Art (PMA) on Congress Square. Located in The Arts district, it is the largest and oldest public art institution in the state. Founded in 1882, this well respected museum houses an outstanding collection of American artists. Maine artists, including Winslow Homer, Edward Hopper, Louise Nevelson and Andrew Wyeth are particularly well represented. You'll also find a few works by European masters, including Monet, Degas, Picasso and Renoir. The collections are spread across three separate buildings. The majority of works are found in the postmodern Charles Shipman Payson building, designed by the firm of famed architect IM Pei. The 1911 beaux arts style LDM Sweat Memorial Galleries and the 1801 Federal style McLellan House Galleries hold the 18th and 19th century American art collection. Note: the museum is open from 10a-6p and is closed on Monday and Tuesday. Not far away on Congress Street is the Institute of Contemporary Art (ICA). This small gallery, attached to the Maine College of Art & Design (MECA&D), showcases an ever shifting slate of modern artists and hosts frequent readings, workshops, pop up shows and lectures. Check the website or call ahead to learn about the frequently updated events calendar. Note: the gallery is open from 11a-5p and is closed on Monday and Tuesday.

Nearby at 109 Danforth Street in the West End is the stately Victoria Mansion. Also known as the Morse-Libby House, it dates back to 1860. The brownstone exterior, elaborate interior design, opulent furnishings and early technological conveniences provide a detailed portrait of lavish living in 19th century America. The former owner of the house, Ruggles Sylvester Morse, was a hotelier in New Orleans and many details, like a stained glass window displaying Louisiana's and Maine's respective state seals, hint at a split identity between the far north and deep south. Morse lived in the house until his death in 1893. A year later, the house and its contents were sold by his wife to Joseph Ralph Libby, a Portland merchant and department store owner. The Libby family occupied the house until 1929. It opened as a museum in 1941 and was named for England's Queen Victoria. It was declared a National Historic Landmark in 1971 for its architectural significance as a particularly well preserved Italianate mansion. Today, Victoria Mansion contains over 90 percent of the original interiors including almost all of the original wall paintings by the Italian born artist Giuseppe Guidicini. Note: the museum is open from 10a-4p and purchasing tickets online in advance is advised.

The Longfellow House is located at 489 Congress Street. The revered American poet Henry Wadsworth Longfellow grew up in this Federal style house, built in 1785 by his Revolutionary War hero grandfather. The house has been impeccably restored to look as it did in the 1800s - complete with original furniture, artifacts and a lovely garden. Admission includes the Maine Historical Society Museum next door, with rotating exhibits about life in Maine over the past few centuries. Note: ask about historical walking tours, offered by the society from June to October. The Portland Observatory can be found at 138 Congress Street. Built in 1807 atop Munjoy Hill, this seven story brick tower was originally used to alert shipowners when their ships were heading for home. Now restored, the observatory has stunning panoramic views of Portland and Casco Bay. Note: admission includes a 45 minute guided tour of the observatory. From there, head to the Eastern Promenade. This stretch of green space includes a small park and East End Beach. It is the perfect spot to relax and perhaps take a chilly swim.

Portland is graced by a handful of handsome lighthouses, including the 1875 Portland Breakwater Light with its Corinthian columns. Dubbed the 'Bug Light' because of its tiny size, it sits in a small park in South Portland with a commanding view of downtown across the harbor. To reach it, cross the Casco Bay Bridge from downtown and continue on Broadway to Breakwater Drive. The Liberty Ship Memorial, across the park from the Bug Light, describes the site's history as a shipyard during World War 2, when more than 30000 people, including about 4000 women, were employed here to build cargo vessels called Liberty Ships. Four miles southeast of Portland on Cape Elizabeth, 90 acre Fort Williams Park is worth visiting simply for the panoramas. Stroll around the ruins of the fort, a late 19th century artillery base, checking out the World War 2 bunkers and gun emplacements that still dot the rolling lawns (a German U boat was spotted in Casco Bay in 1942). The fort actively guarded the entrance to Casco Bay until 1964. A favorite feature of the park is the beloved and much photographed Portland Head Light - the oldest of Maine’s 52 functioning lighthouses. This landmark was commissioned by President George Washington in 1791 and staffed until 1989, when machines took over. The keeper’s house is now a museum which traces the maritime and military history of the region.


Portland has several great places to eat and enjoy a drink or two. Start your day at Becky's Diner, located at 390 Commercial Street. Fishermen and all night revelers enjoy the 4a opening here. At other times, the booths at this wharf side diner are packed with both locals and out of towners. Go with the Hobson's Wharf Special (blueberry pancakes, eggs, bacon, home fries and toast) and attempt to save room for the whoopie pie - a classic Maine treat. Another dynamite spot for a whoopie pie (two chocolate cakes filled with a marshmallow buttercream) is Two Fat Cats. Located at 195 Lancaster Street in the West Bayside neighborhood, this hip bakery serves baked from scratch pastries, pies and melt in your mouth chocolate chip cookies. If you fancy donuts, then you must visit The Holy Donut at 194 Park Avenue. The imaginative sweet treats are made with fresh Maine potatoes and local ingredients at this family owned shop. Flavors range from yummy (maple bacon) to more yummy (dark chocolate sea salt). Note: the store closes when they sell out of the goods, so get there early. One more fantastic locale is Standard Baking Co, found at 75 Commercial Street in the Old Port district (below the Fore Street restaurant). This waterfront bakery specializes in European handcrafted breads and pastries. I highly recommend the morning bun with nuts and the Vollkornbrot (whole grain German brown bread).

For lunch, head to Duckfat at 43 Middle Street. This happening joint is famous for its Belgian fries cooked in duck fat. They are extremely tasty and come with a variety of dipping sauces - do try the truffle ketchup or horseradish mayonnaise. The fancy panini are also excellent and people flock for the poutine. Wash it all down with a marvelous milkshake made from gelato. Note: the restaurant is closed on Tuesday and Wednesday. Just up the road at 78 Middle Street is The Honey Paw. This contemporary bistro serves up Asian inspired noodles and other small bites with local craft beer. Menu highlights include Korean fried chicken, Vietnamese noodle soup and lobster wontons. Note: the restaurant is closed on Tuesday and Wednesday. Next door at 86 Middle Street is the exceptional Eventide Oyster Co. A revival of the great American oyster bar - this place offers pristine Maine oysters and shellfish, the famed brown butter lobster roll, along with a take on classic New England fare. Note: the restaurant is open every day starting at 11a. An additional spot for outstanding oysters is J's Oyster, found on the waterfront at 5 Portland Pier. This much loved dive has some of the best local oysters in town and gives visitors a glimpse of pre gentrification Portland. You can't go wrong with a dozen freshly shucked oysters and an ice cold pint of local Allagash White beer. Note: the restaurant is closed on Sunday.

Located at 414 Fore Street, eclectic Central Provisions is a consistent winner in the Portland haute cuisine stakes. Score a seat at the bar and choose from a masterful small plates menu that swings from tuna crudo to suckling pig. Local oysters, fish and cheese are staples at this rustic, red brick walled establishment. Note: the restaurant also has a cool list of craft cocktails. Chaval can be found at 58 Pine Street in the West End. This stylish brasserie caters to customers looking for seasonal French and Spanish influenced cuisine, ranging from duck rillettes on duck fat crackers to razor clams with breadcrumbs. The cocktails are great and the wine menu is extensive. Note: the restaurant is closed on Sunday and Monday.

For dinner, make your way to Street and Co at 33 Wharf Street. A longtime Old Port favorite, this snug bistro on a cobblestone alley is known for its fresh seafood. The lobster diavolo (in a spicy tomato sauce with pasta) is the house specialty. The wine list truly complements the locally sourced ingredients. Note: the restaurant is open every day starting at 5p and reservations are recommended. Scales can be found at 68 Commercial Street on Maine Wharf. A cavernous dockside warehouse is the setting for this superb seafood restaurant. Windows look out to fishing boats, the raw bar dazzles with local oysters, and the menu tempts with Maine clam chowder, pan roasted halibut and warm buttered lobster rolls. Be sure to save room for the tremendous Maine blueberry pie. Note: the restaurant is open every day starting at 5p and reservations are essential. Located at 288 Fore Street in the Old Port district, Fore Street is the acclaimed restaurant many consider to be the originator of today's food obsession in Portland. Chef Sam Hayward has turned roasting into a high art - chickens turn on spits in the open kitchen as chefs slide iron kettles of mussels into the wood burning oven. Local, seasonal eating is taken very seriously and the upscale menu changes daily. Dinner might consist of a beet and parsnip salad, grilled marinated Atlantic squid and roast bluefish with fennel puree. The large dining room nods toward its warehouse past with exposed brick and pine paneling. Note: the restaurant is open every day starting at 5p and reservations are a must.

End your evening in Portland with a drink or two. Bramhall can be found at 769 Congress Street in the West End. This underground speakeasy has good music, local beers, a ton of bourbon and rum, and a casual crowd of regulars. Another classic joint in the West End is Ruski's Tavern. This down and dirty dive is at 212 Danforth Street and has been open since 1892. Nearby at 150 Park Street is Sagamore Hill. Early 20th century elegance meets a 21st century cocktail menu, plus lots of Teddy Roosevelt memorabilia and a ton of taxidermy at this excellent bar. The interior has an art deco appeal that's tough not to love, especially after a Louisiana Purchase (rye, vermouth, bitters and charred thyme). Note: the bar is open daily from 4p-1a. A chill place in the Old Port is Maps, pinpointed at 64 Market Street. As the name says - there's a bunch of maps decorating the walls at this cool basement bar with rad vinyl records, microbrew beers and good wine. It is warm, inviting and well worth a stop on your Portland pub crawl. Note: the bar sells homemade cakes, which is an utterly unexpected and totally welcome development.

One cannot visit Portland without stopping in to a local brewery. Rising Tide Brewing Company (103 Fox Street) is an independent, family owned brewery that anchors the town's vibrant East Bayside neighborhood. Locals congregate in the parking lot and food trucks visit in summer, from Wednesday to Sunday. Check the website for events (live music, etc). Note: tours are held daily at 3p and also on Saturday at 1p and 5p, and Sunday at 1p. Allagash Brewing Company is located at 50 Industrial Way, about three miles northwest of downtown. Nationally known for its Belgian style beers, it opens its doors for free tours and tastings every day - book online. Note: a couple of smaller breweries offer tastings just across the road, Austin Street and Foundation Brewing. After satisfying your barley and hops craving, head back to town for a stiff drink. The Portland Hunt & Alpine Club can be found at 75 Market Street. This Scandinavian style, minimalist cocktail bar is a two time James Beard semi finalist for 'Outstanding Bar Program.' The setting is spacious, airy and hip - the service is friendly and the cocktails are top notch. Do try a Green Eyes (gin, chartreuse, lime and an egg white). Note: the bar is open from 12p-10p and is closed on Monday. Finish up at my favorite place in town. Blyth & Burrows is at 26 Exchange Street in the Old Port district. This vintage inspired cocktail bar with a maritime theme pays tribute to the two brave captains (Samuel Blyth and William Burrows) who perished after the capture of the HMS Boxer off the coast of Maine in 1813. The two level room features a raw bar and creative small plates in addition to perfectly poured cocktails and impeccable service. I enjoyed a Ship, Captain, Crew (bourbon, lemongrass, spruce tip and pecan wood smoke). Note: the bar is open daily from 4p-11p.


Portland offers a number of places to call home during your stay and there are 2 that I especially enjoyed. Both are in prime locations and provide exceptional service, modern amenities and comfort. The first is The Press Hotel, located at 119 Exchange Street. This boutique, newspaper themed property, set in a classic brick building in the Old Port district is a short walk from the Harbor Fish Market and Longfellow House. The elegant rooms are styled as 1920s writers' offices. They come with wooden floors, vintage desks and marble bathrooms, as well as coffeemakers, free WiFi and flat screen TVs. Upgraded quarters add antique typewriters and separate living areas. Amenities include a posh restaurant and bar, a contemporary lobby lounge and an art gallery.

A second option is Portland Harbor Hotel, located at 468 Fore Street in the Old Port district. This upscale hotel is not far from the Portland Museum of Art and Victoria Mansion. The refined, individually decorated rooms feature private bathrooms with soaking tubs, plus pillow top beds, flat screen TVs and complimentary WiFi. Upgrades add separate sitting areas, fireplaces and views of the courtyard garden. Other perks include a fine dining restaurant and spa treatments.

Portland has scenic vistas, wonderful museums and excellent restaurants. It treated me well and I look forward to returning.


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