A stop in Portland, Maine for a day or two during your New England road trip, or a day trip from Boston, is an excellent way to get acquainted with the history and flavors of the Northeast. Let’s start with a brief history of Portland (I’ve bolded the TLDR):

a brief history

Portland, Maine, has a rich and diverse history that begins long before European settlers arrived. Originally inhabited by the Wabanaki Native Americans, the area was known for its abundant resources, including fish and timber, which attracted settlers in the early 1600s.

The city was officially established in 1786 and was named after the Isle of Portland in England. It quickly became a crucial shipping and trading center due to its strategic location on the coast. Throughout the 19th century, Portland thrived with shipbuilding, fishing, and the transport of goods. The city's waterfront bustled with activity, solidifying its reputation as one of New England's premier ports.

During this time, Portland also witnessed significant growth and cultural development. Many immigrants settled in the city, contributing to its diverse population and fuel the city's economy. The Great Fire of 1866 devastated much of the city, destroying over 1,500 buildings. However, Portland showcased its resilience by rebuilding swiftly, introducing stricter building codes and improving infrastructure.

The late 19th and early 20th centuries marked the emergence of Portland as a tourist destination, attracting visitors with its scenic beauty and recreational opportunities. The introduction of steamships made it more accessible, and the city embraced this new identity by developing hotels, restaurants, and cultural attractions.

In the mid-20th century, Portland faced economic challenges as the fishing and shipping industries declined. However, the city reinvented itself once again, this time focusing on arts, culture, and a burgeoning food scene. The revitalization efforts in the 1970s and 1980s, including the restoration of historic buildings and the establishment of the Old Port district, transformed Portland into a vibrant urban hub.

Today, Portland is celebrated for its charming historic architecture, thriving art community, and a culinary scene that emphasizes local ingredients and seafood. The city's history is a reflection of its adaptability and spirit, making it a unique and welcoming destination for travelers from around the world.

(Generated by AI)

travel times & info

From Boston: 1.5hr-2 (or more depending on traffic)

Parking: There are lots of lots around the city (covered and uncovered). I typically pay between $6-10/hr. There is also 1-2hr free street parking if you can find a spot! Be mindful and don’t leave valuables in your car.

FAVORITE spots TO VISIT & ON MY WANT-TO-GOS

I haven’t been to every possible shop in the city, so I’ll mark the places that are still on my Want-To-Go list.

Portland Head Light - need a car to get here but it’s a beautiful spot on the water with a lighthouse & short coastal walk.

Tandem Coffee & Bakery - You gotta get the biscuit with butter and jam, it’ll change your life.

Weekend Vintage - Vintage clothing store, Want-To-Go
Blind Tiger hotels - Want-To-Go
Yes Books - Used bookstore, Want-To-Go
Strange Maine - Record store
Moody Lords Vinyl/Vintage - Record store
Longfellow Books - Great Indy bookstore
Bread & Friends - Delish bakery/restaurant

Viand Mercantile - Beautiful (although pricy) gift/home shop

Cheese Louise - grilled cheese shop, good vibes
Central Provisions - small plates restaurant, Want-To-Go
Bard Coffee - coffee shop, Want-To-Go
The Highroller Lobster Co - cool vibe, people who like seafood say the lobster is decent LOL