City Guide

City Guide

Portland places
to see, things to do

01

The Arts

Portland Museum of Art

A couple of blocks from The Longfellow, this is the city’s biggest museum, with rotating exhibitions. Tickets required—except on Fridays from 4-8 p.m., when admission is free.

Portland Art Gallery

Open to the public, this gallery space is in the Old Port.

Cove Street Arts

In East Bayside near most of the downtown breweries, this spacious gallery has rotating exhibitions along with community events and music.

SPACE Gallery

A small contemporary art gallery near the Maine College of Art & Design with rotating featured artists and a venue for live music, community talks, and films.

Anderson Gallery

Local artist Robert Anderson’s gallery provides lively colors and whimsical paintings in the Old Port.

First Friday Art Walk

A city-wide art initiative on the first Friday of the month, featuring street art vendors and local businesses hosting special events.

Photo of Portland, Maine

02

Entertainment

State Theatre

This 1,870-seat historic Art Deco–style theatre with Spanish balconies often hosts well-known touring groups.

Thompson’s Point

A gorgeous outdoor music venue on Fore River that has hosted performances from big-name groups—Bon Iver, Leon Bridges, Sheryl Crow, and Brandi Carlisle, to name a few. The State Theatre hosts a summer concert series here to bring the biggest shows outside.

Merrill Auditorium

This venue for the Portland Ballet and the Portland Symphony also hosts plays, classical-style music, dance performances, and more.

Portland Stage

One of Maine’s largest fully professional nonprofit theaters offers plays, musicals, and other performances.

Blue

A low-key jazz club with open-mic nights and live performances.

One Longfellow Square

A smaller nonprofit venue for live music, performing arts, speakers, and other events.

03

Local Dining

Twelve

At this critically acclaimed restaurant run by Colin Wyatt, formerly of Eleven Madison Park, New York skill meets Maine comfort and flavors. Near the waterfront, it has a patio for summer dining.

Leeward

A James Beard Award nominee, Leeward offers delicious house-made pastas in an airy yet comfortable space.

Crispy Gai

Open since 2021, Crispy Gai features a menu of Thai and Southeast Asian flavors. A great place for date night, their platters of hat yai fried chicken, fried rice with Chinese sausage and pad see ew are not to be missed.

Wayside Tavern

Right across the street from The Longfellow and next to The Francis Hotel, Wayside Tavern is a cozy yet refined European-inspired eatery with classic dishes that are comforting yet creative.

Fore Street

Keeping traditional and inspired entrees in action amidst the rise of shared plates, Fore Street boasts a comfortable yet slightly industrial vibe with its brick walls and exposed beams. The owners also own Scales and Street and Company, two fabulous restaurants also in the Old Port.

Solo Italiano

With house-made pasta and bread as well as a great wine list, Solo Italiano in the Old Port offers authentic Italian cuisine fresh from the farm and the sea.

Central Provisions

Shareable delights on small plates in the Old Port. A bit tight on space, but an intimate atmosphere with moody lighting and delicious cocktails.

Via Vecchia

Go for the décor, and stay for the shareable plates and cocktails. This Italian-inspired eatery in the Old Port offers unique flair, with lush green velvet booths, gold silverware, and marble bar tops.

A lighthouse in Portland, Maine

04

Attractions

Portland Head Light

The classic Maine lighthouse—and a must-see. Here you’ll find sweeping ocean views and trails to walk along the cliffs. Stop at Bite Into Maine (open seasonally) for one of our favorite lobster rolls in the Portland area.

Eastern Promenade

On the other side of the peninsula that juts out into Casco Bay, this walking/biking trail wraps around the water. Great for a stroll or a bike ride starting at the end of Commercial Street and taking you around to East Bayside, which is home to many breweries.

Western Promenade

A couple of blocks west from The Longfellow, this grassy tree-lined park offers amazing sunset views. Stroll through the historic neighborhoods on the way there and admire the gorgeous architecture and manicured lawns.

Spring Point Lighthouse

Just a short drive over the bridge into South Portland, near Willard Beach and on the Southern Maine Community College campus, this lighthouse has a long rock walkway out to the edge of the headlight. Be sure to wear sturdy shoes!

Bug Light Park

Also just a short drive over Casco Bay into SoPo, this grassy park offers picnic tables, a small lighthouse, and views of the Portland peninsula from the other side of the bay. Great for picnics.

Higgins Beach

A top surfing destination in the area, Higgins Beach is between Cape Elizabeth and Scarborough; it has incredible sweeping ocean views, a sandy beach, and is dog-friendly at certain times. It’s under 20 minutes by car from The Longfellow.

Kettle Cove

Located in Cape Elizabeth and about a 15-minute drive from The Longfellow, this cove offers views of the ocean and islands in the distance, along with the classic rocky Maine coastline.

Victoria Mansion

Built between 1858 and 1860, this is a national historic landmark you can tour to see furniture and décor from the era. It’s located right behind the Portland Museum of Art.

05

Hikes & Walks

Back Cove Trail

A 3-mile walking trail around Back Cove—an inlet of Casco Bay. Great for running, walking and chatting, or biking. If you’d like to lengthen your journey, you can also connect to the Eastern Promenade Trail.

The Greenbelt

A biking/walking trail through South Portland. Follow the Greenbelt Trail on bike or by foot over the Casco Bay Bridge—the path can take you to the end of the South Portland peninsula and the Spring Point Light House, Bug Light Park, or Willard Beach. Stop along the way for great skyline views of Portland!

Fore River Trail

A short raised wooden walkway trail along the river, quite close to downtown Portland.

Fore River Sanctuary

This larger hiking area is slightly farther out, but features a waterfall and views of the river from its dirt and wooden walkway trails.

Robinson Woods Nature Preserve

This wooded trail in Cape Elizabeth is near the coastline and offers wonderful sights and sounds.

Mackworth Island

Just north, a bit toward Falmouth, this island is accessible by car over a small bridge and has looped trails that go around the perimeter of the island. It’s known for its fairy circles—and hikers are encouraged to create fairy sanctuaries of their own.

Bradbury Mountain State Park

A bit of a drive—about 30 minutes from the city—but well worth it for slightly more rigorous hiking (though not that rigorous). Here you’ll find nice views of the area below.