Must Dos of October in Boston

If you're looking for something to do this October, don't worry – Boston has you covered. This city is packed with events and activities that are perfect for the spooky season. Whether you're looking for a family-friendly event or something more adult-only, we've got you covered. Keep reading to learn about some of the coolest things happening in Boston this October!

Boston Harbor Cruises

The Boston harbor cruises have a little something for everybody from all walks of life, from being able to appeal to a student demographic who just wanna get their party on for a night; all the way to appealing to a classic Nuclear family who wants to see the foliage in a way they've never experienced it before. All the different types of cruises make for a lot of fun choices to be made with your family, should you check out the islands and the fort, or go looking for whales just off the coast? All these and more tours leave from the city harbor all day every day and really bring out the fun of Boston.

Columbus Park Fall Festival & Pumpkin Patch

The Columbus Park Fall Festival and Pumpkin Patch is a great event for families with young children. This event takes place in the North End of Boston and features games, rides, food trucks, and – of course – a pumpkin patch. Kids will have a blast at this festive event, and adults will enjoy the food trucks and live entertainment. And ultimately it's a great way to escape the dreary trudge through October by Brightening your weekend and giving you a great chance to try all the Apple Cider and Pumpkin Spiced treats New England has to offer in one great kid-friendly place!

Head of the Charles Regatta

The Head of the Charles Regatta is one of THE biggest events to happen in the fall. With rowers of all classes, ages, and skills coming from all over to compete against each other and show who can move a boat quicker. Although it sounds about as exciting as NASCAR it's actually thrilling, especially with the atmosphere of fun and camaraderie that you see the competitors embody and then of course their supporters as well. Parents will cheer their kids on, and spur their rivals to greater heights, it really is a fun and exhilarating experience all around and if you get the chance you should go down and support your local teams!

Open our Doors Festival (Fenway area)

The Open our Doors Festival is a great way to check out all the different businesses in the Fenway area. This event takes place over the course of two days and features discounts, giveaways, and other fun activities at participating businesses. It's a great and fun opportunity to explore the Fenway area and find some new places to shop, eat, and drink. So if you're new to Boston, or just haven't been out for a few years this is a great way to see what's new and happening in probably one of the busiest places to be in Boston.

The Theater!

And of course, we can't forget the theater! Boston is home to some of the best and oldest theaters in the country, and October is a great time to catch a show. Check out what's playing at the Huntington Theater Company, or take in a musical at the American Repertory Theater. The options are endless, and while nothing will compare to the grandeur of Broadway Boston more than makes for that with talented actors, and amazing set pieces. We recommend checking out Hairspray at the Boston Opera House October 18-30

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