Wicked Fall Guide

Wicked Fall Guide

Wicked Fall Guide

This Fall will have you falling in love with our beautiful city all over again! That is if you check out any or all of these 9 fabulous fun Fall things to do in Boston. I enlisted some help from  Time Out Boston, who had some great suggestions, as well as Boston Discovery Guide. Here, I’ve created a list for you that is definitely bucket worthy.

October will be here before you know it, so make your plans to visit Boston. Whether it’s a day trip or an overnight, you can squeeze in a lot in a small amount of time, or a little in a lot of time. Beer gardens that popped up in the Spring will soon be shutting down, so enjoy crisper air to come in the next couple of months outdoors. Take advantage of patio dining, as many stay open through October. Get in the spirit of Halloween. Do a foot tour, a food tour, or a tavern tour. Join a group or do it all on your own.

Fall weather is perfect for a bike ride, a whale watch or a hike. There are so many places in the greater Boston area to do all of those things. Plus, when a sweater or light jacket doesn’t cut it, take your fall fun indoors. Visit a museum, explore a new neighborhood, see a concert or take in a musical in the theater district.

With all of our history, arts and beautiful landscape in Boston, there is bound to be something to tickle your fancy. Food tours and walking tours are a great way to learn more and love more about our city. There are plenty of options laid out for you here. So make your plans. Discover 9 fabulous fun Fall things to do in Boston this year.



  • 1. Color Your World With Photos of Foliage

    October is always optimal foliage time around Boston, and one of the best places to capture the colors of Fall is at the Public Garden. Leaves of red, gold and orange decorate the Lagoon in Boston’s Public Garden.  Those beautiful weeping willow trees reflect so perfectly in the water.

  • 2. Bike Boston

    Ok, so you may have to wear a slightly heavier jacket for this, but biking Boston is a great way to see the city without the hassles of parking. Of course Blue Bikes are always a good option too. And there are bike tours! One tour is led by Urban Aventours (109 Atlantic Ave, just across from Christopher Columbus Park in Boston’s North End). There are several a day and a few options of tours, as well. 

    Urban AdvenTours | Boston Bikes: Rental, Store, & Tours

    Join Urban AdvenTours Boston bikes to shop for bicycle rentals and bike tours! We have eBikes, road bikes, and more! Book your Boston bike online now.

  • 3. Showtime

    See a theater show, a concert or a comedy show. October and November are perfect months to take your nighttime fun indoors. Boston is booming with great venues for music and theater. Comedy shows are popping up all over the place, too. Boston Discovery Guide is offering a discount: Enter DISCOVERY10 to save 10% on TicketLiquidator and TicketNetwork tickets through 12/31/2024.  Here’s a few ideas:


  • 4. Food Tours

    There are quite a few food tours from the North End to South End. Chinatown to Downtown. I absolutely loved my North End food tour with life long local, Bobby Agrippino. Whatever you choose, you know it will be good. How could you go wrong with delicious food in a beautiful city! Food tours are another great way to explore and learn about Boston (even if you’ve lived here your whole life).

    Boston, MA Tours | Home | North End Boston Food Tour

    Experience an authentic Boston, MA tour today. North End Boston Food Tour will guide you through North End like a local. Schedule with us today.

  • 5. Cheers To Beers... and Beer Gardens

    Before they close up the taps, and take down the tents, spend a sunny fall afternoon “sipping a world-class beer beneath an umbrella in a beer garden” (Time Out Boston). The Rose Kennedy Greenway hosts Trillium Garden on the Greenway. It was Boston’s first open-air beer garden in a public park, and it’s now a staple in our city. Cisco Brewers in the Seaport has a beer garden open through October 15. Nantucket’s favorite brewery has a huge outdoor area for sipping and noshing. And of course it’s a great place to catch the game. 

  • 6. Hike It

    All the Autumn vibes are best caught walking the earth. No need to travel far, there are many excellent options right here at home, without having to fill up the tank. From trails to hills, the Boston area has it all, including the great Blue Hills Reservation on the Milton/Canton liner. Also check out the Middlesex Fells Reservation. Or hit the Arnold Arboretum, for a more relaxing journey. They can all be reached by T or bus. 

  • 7. Hope On the Halloween Bandwagon

    Although Salem isn’t terribly far from Boston, it can get terribly crowded. You can get your spook on a little closer to home. Boston has many historic graveyards and there are tours for that! The most famous of such tours is the Ghosts and Gravestones tours, But there are certainly others…

    Halloween Boston Events 2024 - Ghosts, Parties, Tours, Witches - Boston Discovery Guide

    Halloween in Boston means ghost tours and events, witches, haunted graveyards, a gore-filled comedy show, where to shop for costumes, pumpkin decorating! Find out more.


  • 8. Visit a Museum

    Boston’s Isabella Stewart Gardner Museum is world renowned, with it’s gorgeous, lush indoor garden and historical art displays. The perfect place to get away on a chilly fall day. The Museum of Fine Arts always has something brewing, from classes to exhibits and crafting. My personal favorite museum…Fenway Park! Well, it’s a living, working museum of sorts and always fun to walk around the halls that Ted Williams, Big Papi, Babe Ruth and Pedro Martinez built. You’ll find quite a few tours that will take you to the park. Or just go on your own and sign up through the Red Sox website:

    Tours of Fenway Park | Boston Red Sox

    Public and private stadium tours of Fenway Park, the home ballpark of the Red Sox.

  • 9. Watch for Whales

    Whales are still dancing around Boston Harbor and beyond, even though summer is in the tailwind. In fact, prime whale watching season is said to bee March through November. So get out there on the great blue sea before the chill gets you. Choices? Oh, you’ve got choices with cruises departing from Boston and surrounding harbors, most of which make their way for Stellwagen Bank, considered one of the optimal spots for watching whales in the world.

    Whale Watching Boston: 6 Local Boat Tours for Seeing Whales

    Get out on the open water and see some majestic mammals firsthand with these tours for whale watching near Boston

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