In the tangle of downtown Portland, Monument Square feels like the city’s living room-where East Bayside meets the Old Port’s salty breeze. Glance around and you’ll spot the Time & Temperature Building blinking updates, the stately Fidelity Trust Building, and the Portland Public Library’s main branch all lining up along Congress Street. Brave souls even call One Monument Square and One City Center their professional homes here.

Center stage, where old City Hall once huddled, stands the Soldiers and Sailors Monument, unveiled in 1891 to honor Maine’s Civil War heroes. Locals affectionately dub her “Our Lady of Victories”- a bronze warrior-woman draped in armor and robes, clutching a neatly furled flag in one hand and a mace and shield in the other. At her feet, trios of soldiers and sailors freeze in bronze display, forever caught between orders and the next battle.

Chisel in hand, sculptor Franklin Simmons breathed life into the figures while New York architect Richard Morris Hunt crafted the monument’s sturdy granite plinth. Portland’s own Francis H. Fassett first landscaped the grounds-though time has since sent those original flowerbeds to the history books. All things considered, Monument Square earned a spot on the National Register of Historic Places in 1998.

Pull up a bench, let the city swirl around you, and tip your hat to the legends immortalized in stone and bronze.

Shipyard Brewing Company, founded in 1994, is a cornerstone of the local vibrant craft beer scene and the largest brewery in Maine. With roots dating back to 1992 as the Kennebunkport Brewing Co., Shipyard was originally launched by Fred Forsley and Alan Pugsley at Federal Jack’s Restaurant and Brew Pub in Kennebunk.

As demand for their brews outgrew their humble beginnings, Forsley and Pugsley expanded, opening Shipyard Brewing Company in Portland, on the site of the historic Crosby Laughlin Foundry. Today, Shipyard isn’t just a single brewery-it’s a powerhouse with multiple brands, including Sea Dog Brewing Company and Casco Bay Brewing Company, and it ranks as the fourth largest microbrewery in New England.

Shipyard’s portfolio is impressive, brewing over 81,000 barrels of ale and distributing products to 40 states by 2008. Known for its quality craftsmanship and wide variety of beers, the brewery offers everything from its classic brews to seasonal and experimental varieties at its Tasting Room, which features 20 rotating beers on tap.

Beyond just beer, Shipyard is also home to Capt’n Eli's Soda, providing a refreshing selection of soft drinks. The brewery, a proud family-owned business, continues to thrive in Portland while staying rooted in tradition and fueled by innovation. Visitors can sip on a flight of Shipyard’s award-winning brews while enjoying delicious pizzas, pretzels, and sandwiches, and then shop for some Shipyard swag to remember the visit.

Active in local community projects, Shipyard’s commitment to Maine extends beyond beer. Their collaborative spirit with other breweries and involvement in various charitable efforts makes them a beloved institution.

The United States Custom House is basically Portland’s granite love letter to maritime trade. Built between 1867 and 1872, it rose from the ashes of the Great Fire with one clear mission: keep the booming harbor in check and the customs business running like clockwork.

Crafted from rugged New Hampshire granite and topped with a slate roof tough enough to laugh at sparks, the Custom House was fireproof by design-a cautious nod to the inferno of 1866. Its I-shaped layout and three sturdy stories give it the kind of presence that says, “business first, beauty second”-though it manages to pull off both with ease.

The style is part Renaissance Revival, part Second Empire, and all confidence. Two square towers capped with slightly sloping roofs crown the building like a pair of granite crowns, flanked by Corinthian pilasters that add a touch of theatrical drama. Venetian-style arched windows soften the heavy granite walls, each topped by its own shallow pediment, like architectural eyebrows raised just high enough to impress.

But the Custom House is more than an elegant façade-it’s a symbol. This was the gatekeeper of Portland’s economy, where the Atlantic world funneled into ledgers, tariffs, and fortunes. Today, listed on the National Register of Historic Places, it’s still one of the city’s sharpest dressers. Granite, symmetry, and just enough French swagger-it’s ready to collect tariffs, throw a party, or simply remind you that Portland’s pride was once measured in tall ship masts.

The City of Portland boasts a rich fishing heritage, with Custom House Wharf standing as an essential part of its historical narrative. While numerous wharves in Portland have succumbed to modernization and diverse purposes, Custom House Wharf has remained largely unchanged. Positioned by the waterfront, opposite Portland's renowned Custom House Building, this wharf has long served as a haven for fish dealers and processors.

Constructed during the 1930s, the wharf's two extensive rows of weathered buildings have accommodated fish dealers, small enterprises, ferry terminals, and restaurants throughout the years. Ownership of this wharf has remained within a single family for over 90 years, resulting in minimal development and preserving its charming allure. Fishermen and lobstermen still moor their boats here, while also engaging in repairs and net mending. Moreover, countless tourists frequent this wharf, capturing photographs of its picturesque scenery.

Upon entering the Harbor Fish Market, visitors are greeted with a continuation of the wharf's historic ambiance. Since its establishment in 1966, Harbor Fish has undergone various updates, yet a glimpse beyond the new fish cases and coolers reveals the essence of the old store. Fishmongers bustling behind the counters and within the office, an abundance of fresh fish, competitive prices, and knowledgeable staff eagerly prepared to assist customers-these elements encapsulate the essence of Harbor Fish Market.

Casco Bay is a scenic inlet of the Gulf of Maine stretching from Cape Small in the east to Two Lights in Cape Elizabeth on the west. The city of Portland, Maine’s largest, lines the bay’s southern edge, with the bustling Port of Portland nestled within its waters.

Known for its many islands-often called the Calendar Islands due to the popular myth that there are as many islands as days in the year-Casco Bay actually contains between 136 and just over 200 islands.

Historic lighthouses such as Halfway Rock and the iconic Portland Head Light mark the bay’s entrances, guiding mariners into Portland Harbor, a busy working waterfront that welcomes cruise ships, cargo vessels, and oil tankers alike.

Beyond its maritime significance, Casco Bay and Portland offer rich cultural and culinary experiences. Portland has earned the title of “America’s Foodiest Small Town” thanks to its vibrant seafood scene and diverse ethnic cuisine, drawing food lovers from near and far.

The city also boasts a lively craft beer culture, with over 15 breweries crafting local favorites. Alongside its gastronomic appeal, Portland is a thriving arts hub, home to the Portland Museum of Art, which features works by internationally renowned and Maine-based American artists, as well as world-class performing arts organizations like the Portland Symphony Orchestra, Stage Theatre, and Portland Ballet.

Imagine a neighborhood that feels like a living history exhibit-but one where you’re invited to sip craft beer and nibble lobster rolls along the way. That’s the Old Port Exchange, Portland’s beloved old-timer district defined by snaking cobblestones, 19th-century brick facades, and wooden piers where fishing boats still tie up.

Wander down Wharf Street and you’ll see why this strip has its own magnetic pull. Candlelit tables spill onto the cobbles, giving seafood feasts a glow that gold-plated floors could never match. Boutique shops line the street between rustic pubs, while galleries showcase local artists whose work is inspired by the city’s history, textures, and everyday rhythm. By evening, the Old Port hums with energy, as locals and out-of-towners converge on cozy taverns and rooftop lounges.

But there’s more to this historic quarter than nightlife. Post Office Park and Tommy’s Park offer leafy respites if you need to swap your bar stools for a bench. A quick jaunt down to Bell Buoy Park, found beside the Casco Bay Ferry Terminal, will reward you with sea breezes and ferryhorn fanfares. And don’t miss the tail-end of the Eastern Promenade Trail, which funnels right into the Old Port-you can stroll off your morning pastry seamlessly.

What makes the Old Port truly enchanting is its blend of old and new: centuries-old warehouses reborn as sleek restaurants, centuries-old stones that still feel alive under your steps, and a waterfront vibe so authentic you might taste the salt in the air.

Victoria Mansion is the city’s very own architectural gem-a dazzling example of American residential design from the mid-19th century. Built in 1860 as a summer escape for Ruggles Sylvester Morse, a hotel magnate who struck it rich in New York, Boston, and New Orleans, this mansion oozes grandeur and history.

Designed by Henry Austin, this brownstone Italianate beauty got that cool, asymmetrical flair with a four-story tower, overhanging eaves, and verandas that practically beg you to relax with a cool drink. Inside, the mansion’s charm continues with intricate frescoes and three-dimensional wall art, all thanks to the talented Giuseppe Guidicini.

The mansion had a cozy family feel until 1928, when the last member of the Libby family left. After the economic hardships of the Great Depression and the disastrous 1938 Portland flood, the house faced potential demolition (seriously, a gas station was on the cards). But, thankfully, the mansion was rescued in 1941, and lovingly restored to honor its royal inspiration-Queen Victoria.

Now listed on the National Historic Register, Victoria Mansion is a museum that transports you straight back to the opulent 19th century. It's a true testament to Portland’s rich history and an absolute must-see for anyone who enjoys a bit of grandeur, with a side of history-and maybe royalty sprinkled in.

Allagash Brewing Company, founded in 1995 by Rob Tod, specializes in Belgian-style beers and has grown into one of the most respected breweries in the United States. Tod’s vision was to fill a gap in the American beer market, offering authentic Belgian-style brews when German and British styles dominated.

The brewery’s flagship beer, Allagash White, is a Belgian Witbier brewed with wheat, Curaçao orange peel, coriander, and other spices. Its unique flavor profile and traditional bottle-conditioning process-featuring two fermentations, including one in the bottle-give it remarkable complexity and a smooth, effervescent character.

Allagash is also known for pioneering the use of a traditional coolship in the US, enabling spontaneous fermentation with wild yeasts to create authentic Lambic-style beers.

The brewery offers over 15 beers on draft year-round, alongside housemade cider and wine, and features a cozy, temperature-controlled indoor space with additional outdoor seating. Visitors can enjoy fresh seafood and other local treats from the onsite food truck, including the award-winning lobster rolls from Bite Into Maine.

With numerous medals from top international beer competitions, Allagash Brewing Company stands as a beloved cultural and community hub in Portland for beer lovers seeking genuine Belgian-inspired brews.