The Weekly Getaway: Halloween in Boston
Travel Guides

The Weekly Getaway: Halloween in Boston

Anastasia Hassiotis | 26 October 2016
Best time to go:
May-Jun and Sep-Nov
Ideal trip duration:
3 nights

Boston is probably one of the few cities in the US which are beautiful throughout the year. However, fall is definitely my favorite season and my reason can be easily justified. As the leaves turn color and fall off the trees, Boston Common’s beauty is unforgettable. Along with its historic architecture, walking around the park will definitely make you feel like a child again!


Back Bay, Fenway and Beacon Hill

Wander around the luxury shopping district of Back Bay visiting boutiques and little stores on Newbury Street, taking a break in between at its various coffee shops and restaurants. In case you’re one of those who enjoy a good walk with a hot beverage, then definitely visit LA Burdick for a hot chocolate to go and hit the road again.

If the weather is too cold for you but still looking for that shopping spree day, then Prudential Center, right next to Copley Square, will do. In addition, a good day indoors can definitely be spent at The Museum of Fine Arts, which holds one of the most comprehensive collections in the world and possesses materials from a wide variety of art movements and cultures.

No matter whether you love art and architecture or you know nothing about them, a walk in the most beautiful neighbourhood in Boston, Beacon Hill,  will make you appreciate nature and the famous brownstones’ architecture. Let your self get lost in the narrow streets, enjoy the decorated house entrances with pumpkins and all sorts of halloween extravaganza and feel the nature through the fallen leaves surround you.



Georgetown cupcakes


Georgetown cupcakes

Eggs on toasted brioche, with maple ham and cheese at The Paramount


Eggs on toasted brioche, with maple ham and cheese at The Paramount


Waterfront and Cambridge

Waterfront is a location that could be advantageous for many families as it offers the Faneuil Hall, a marketplace usually crowded, depending on the time of the day, which offers shopping and dining. During the weekends there is also a carousel that kids – why not even parents – can ride and have fun. In addition, you can spend the rest of the day by having a stop at the Aquarium, located just a few minutes away from Faneuil Hall.

Plan a day to cross the bridge and visit Cambridge’s hot spots. Visit Harvard University’s open campus with lots of historical buildings and enjoy Harvard Square which is usually full of young crowd. In case you get hungry you can always try, perhaps the most famous restaurant in the area, Mr. Bartley’s burger cottage. There’s usually a queue but it’s definitely worth the experience.


Building inside the Harvard campus


Building inside the Harvard campus



  • Boston Public Garden and Boston Common – one of the most lush and colorful parts of the city; you’ll see many busy workers taking a break during lunch. Also nice for a quick job in the morning
  • Faneuil Hall – marketplace located near the waterfront offering unique shopping, dining and entertainment experiences. Fun to walk around the shops (visit the picturesque Christmas shop) and enjoy lunch/early dinner at one of the many restaurants in Quincy Market. Most of the times there are street dancers or jugglers that create a festive atmosphere
  • Boston Museum of Fine Arts – located very centrally in Copley Square, this museum is probably the best option if you visit only for a few days. Nice permanent collection with pieces from ancient Egyptian to contemporary. Also features interesting exhibitions from time to time
  • Beacon Hill – this neighbourhood is amazing and mostly residential; ideal for some relaxed strolling in the weekends, also featuring tasty spots for breakfast/brunch (see below)
  • Newbury street – beautiful wide street with many brownstones, ideal for window-shopping (or even a splurge!) – features many boutiques but also some quick bite restaurants and cafés


  • Ames Boston Hotel – combination of old and modern at its finest. Housed in a historical building of the Financial District, moments away from Beacon Hill, Faneuil Hall and Government center, this hotel offers a luxury cozy atmosphere
  • XV Beacon – luxurious boutique hotel located on the heart of Beacon Hill attached to the famous Mooo steakhouse. If you’re looking for great service, modern sophisticated interiors and perhaps a fireplace in your room then you’re good to go!
  • Kimpton Nine Zero Hotel – Spot-on location overlooking Boston Common, this hip hotel is all about colors, patterns and comfort.


  • Grill 23 & Bar – proper American white-cloth steakhouse with the finest steaks and a classic signature dessert… milk and soft-baked cookies! Read our full review here
  • Yvonne’s – new American restaurant with beautiful interior and great for group dining
  • Shojo – casual Asian fusion restaurant. Fan of baos? That’s your place! Read our full review here
  • Bar Mezzana – coastal Italian restaurant with amazing pasta and crudo options
  • Porto – Mediterranean tapas food along with great balcony to enjoy on sunny days
  • Mooo – juicy steaks; don’t say no to their bread rolls – yum!
  • Hojoko – fun casual Japanese tavern – no reservations
  • Little Donkey – global small plates from James Beard Award-winning chefs Ken Oringer & Jamie Bissonnette
  • Barcelona – tapas wine bar. Definitely order the truffled bikini, patatas bravas, hanger steak and jamon Serrano
  • LA Burdick – best hot chocolate in Back Bay, to go!
  • Georgetown cupcakes – colorful, fluffy and yummy; must try on Newbury street!
  • Brunch
    • Tatte Bakery – great place for a breakfast/brunch where locals hang out; eggs are amazing but also have some nice dessert options! Read our full review here
    • The Paramount – famous for their American breakfast (think maple ham on toasted brioche!). First queue, then sit and eat – amazingly efficient and ideal for a quick bite
    • Mistral – one of the best brunch places – don’t forget to order the Valrhona Hot Chocolate with hand-crafter marshmallow, the eggs Benedict  and the milk chocolate pancakes
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