A trip to Vacationland: Portland, Maine

Written by Libby Chandler

Known affectionately to Americans as Vacationland, Maine’s largest city is not so well known outside of North America. Just a 2-hour bus journey from Boston, the comparatively small city boasts culture, history, and some of New England’s most beautiful scenery. Having spent 9 months studying abroad there, I may be biased – but Portland is one of the hidden gems of the East Coast to foreign travellers. 

With hot, humid summers and beautifully brutal winters, Maine experiences weather at both ends of the spectrum year-round. Having lived there from August to May, I would consider the best time to go to be September/October, or possibly late April/May. This way, you will experience milder weather with warm and cool spells and relatively little rain. You will also narrowly avoid tourist season – American schools often break for summer between late May and mid-August, and Maine is a popular destination for Americans wishing to holiday within the country. 

As Maine is famous for its kaleidoscope of burnt oranges, rusty reds, and bright yellows in the autumn (trust me, it’s worth having a google of autumns in Maine), October might be preferable if you want to feel like you’re in an episode of Gilmore Girls. Of course, if you don’t mind braving the cold, the winter season is also a possibility. Portland is not too far from ski resorts, may be an ideal spot for keen skiers. Even if you’re not into winter sports, Maine is simply stunning even when coated in thick layers of glittery snow – and Portland is no exception. During this period, you’ll undoubtedly have run of the city to fully appreciate the wonders of New England’s finest.


Although a car is preferable to travel around the rest of Maine (a surprisingly large state in the northernmost corner of America’s East Coast), it is not necessarily needed for sightseeing around Portland. The city has a central hub in the Downtown and Old Port area and also has extensive bus links around the rest of the city for only $2 a trip. While probably more expensive, it is certainly worth spending the extra money to stay amongst the red brick and cobblestones of the Old Port.

Part of its New England charm comes from the relics of Portland’s colonial past, but what is surprising to the modern eye is how untouched the centre is by big businesses; sure, there might be a Starbucks here and there, but the Old Port is packed with independent businesses and restaurants, something that residents there are very proud of. Famous for its seafood, particularly lobster, Portland boasts a vibrant and delicious food scene that ranges from traditional New England dishes to Lebanese and Korean cuisine. Plus, there are plenty of cute coffee shops, pubs, and cocktail bars to spend some downtime in. 

Possibly one of the best ways to spend a day in Portland, though, is by leaving the mainland. Just a short 15-minute ferry ride (for which the tickets are surprisingly cheap) are the Casco Bay Islands – a collection of islands scattered around the port. You can visit each one, or even take the mail boat ferry around them all (many of the islands are inhabited!), but the biggest and most popular to visit is Peaks Island. The island remains charming and idyllic even without sunshine – staying remarkably peaceful despite the occasionally busy ferry trips. Golf carts and bikes are available to rent in order to get around the island but the budget option of going on foot is easily doable. Peaks is one of those places that feels straight out of a romcom, except it might just be the island itself that characters fall in love with. 

If I’ve managed to pique your interest in visiting America’s Vacationland, then my final suggestion would be to explore further up the coast of Maine. Hire a car and drive up to Bar Harbour and Acadia National Park, which deserve a dedicated article themselves. The drive up will take you through quaint New England towns that feel just like film sets and along a deep blue coastline overrun with pine trees (Maine is the Pine Tree State, after all).  I may be biased but I truly believe that everybody deserves to cross the Atlantic and visit this magical state

Libby Chandler is a final year BA American Studies student from Cardiff, who spent her year abroad in Portland, Maine. Her main areas of interest are women’s rights, specifically reproductive rights in the Americas, a topic she is currently writing her dissertation on. Aside from this, she enjoys travelling, reading about Greek mythology, and has an interest in film and television.

Photography by Libby Chandler

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