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Stuart Messham
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Steeped in history with tonnes of cool, contemporary touches, Boston is a beguiling mix of old and new and a big hit with tourists all year round. So let’s take a seasonal stopover in The Puritan City and see what it has to offer…
The idyllic wintry fun never stops on Frog Pond. Just make sure you can!

Throw some icy shapes on the Frog Pond in Winter

There’s lots to appreciate about Boston in the colder months – the rich colours of the trees in Fall, the delicious pumpkin-spiced lattes, the artisanal Christmas market – but there’s nothing quite as traditional as donning a pair of skates and cutting some slippery shapes on Boston Common’s Frog Pond.

It’s something of a tradition in “the Cradle of Liberty” to take a seasonal icy spin and you’ll find every level of skater throwing shapes here, from nervy newbies to blasé backwards skaters to liberated locals spinning and jumping their way around the rink.

It’s plenty big, so there’s room for everyone, but it does get busy, so be prepared to queue. And remember: no matter your level of performance on the slidey stuff – pride should certainly be put to one side! – a warm, comforting treat always awaits at the on-site snack bar afterwards.

So close to the city and yet so far removed, hiking in Boston really is an unexpected joy.

Hike your merry way around The Hub in Spring

A saunter along the Freedom Trail is a great way to enjoy the history and culture of Boston and an excellent starting point for energetic newcomers who want to breathe the Boston air and feel the city vibe. Take a small jaunt outside of the bustling centre though and you’ll be stunned at the amount of rollicking rambles “America’s Walking City” has to offer.

The 7,000-acre Blue Hills reservation is a veritable hiker’s paradise with 125 miles of glorious trails to enjoy. Want to wallow in a scenic wooded preserve? No problem. How about exploring some Instagrammable waterfront trails? Sure thing. Wherever you choose to wander, it's a fabulous antithesis to the chaos of the busy city, which, by the way, you can look down upon in awe if you scale to the top of the Great Blue Hill.

(The White Mountains and the Appalachian Trail offer more scope for two-legged adventure a little further afield.)

Locally-sourced lobster rolls and oysters. Simple food that's simply delicious.

Enjoy the world’s best lobster rolls and freshest local oysters all year round

There is no ideal time to sample the fresh seafood of Boston because it’s beyond delicious all year round.

Fresh oysters are a staple of the city’s culinary scene and the best ones – including locally-sourced varieties like the Wellfleet, Cotuit and Glidden Point – can be found at the Union Oyster House, a seafood institution which was opened in 1826 and continues to thrive to this day. Oyster happy hours are a thing here too, so you can sample these briny treats at extremely affordable prices.

Lobsters are also sourced locally from cold waters along the New England coast and trying a fresh lobster roll is an absolute must during your stay. Belle Isle Seafood in Winthrop is the perfect locale for a no-frills lobster roll experience with more upscale varieties available at many eateries across town.

Fenway Park: hard to get in, but you won't want to leave.

Enjoy a game at the world-famous Fenway Park

Boston has many nicknames – as you’ve probably gathered from this piece – one of which is “Titletown” and another of which is the “City of Champions”. Why? Because of the glorious exploits of its world-famous sports teams, one of which plies its trade at the illustrious Fenway Park, the Boston Red Sox.

It’s the oldest ballpark in Major League Baseball and, unfortunately, one of the smallest, meaning tickets for big matches are notoriously hard to come by. However, acquiring them is possible and should you get the chance, it’s an experience that’s amped up tenfold atop the stadium’s most distinctive feature, the 37ft high wall on the left field known as the Green Monster.

Course, if baseball’s not your bag, you can always take in the brilliant Boston Celtics at TD Garden. Whichever you choose, the atmosphere will be raucous, the entertainment ramped up to 11 and the expectation of the crowd set to "HIGH".

Come on, Boston!