Inn @ St. Botolph Blog

Best Fall Activities in Boston

Posted by Inn at St. Botolph on Sep 15, 2016 5:52:54 PM

We're here to help you make the most out of your fall trip to Massachusetts! To assist with your trip planning, we've pulled together 20 of our favorite fall activities in Boston and beyond. There are plenty of things to do in the city during the season as well as day trips, just a short train ride or drive away. Here's what we're most looking forward to this fall: 


1. Head of the Charles Regatta
Saturday, October 22nd – Sunday, October 23rd 

The Head of the Charles is a 2-day rowing event that draws thousands of athletes from across the world to compete and over 300,000 spectators join to watch. Always the third weekend in October, this year it falls on Saturday, October 22nd & Sunday, October 23rd. Spectators can sit and watch the races or stroll along the Charles River. Many sponsors and food vendors set-up along the river and we recommend bringing a picnic blanket so you can sit and eat while you watch. 

2. Paddle the Charles River
On a nice day, we suggest renting a boat from Charles River Canoe and Kayak. It’s a perfect activity for first timers and experienced paddlers alike. Paddling on the river allows for a whole new perspective and a stunning view of the city. They charge you by the amount of time that you’re out on the water, so you can easily venture out on your own and choose how many hours you’d like to spend. For those who want to go with a group, there are also guided tours. You'll get an especially beautiful view if you go when foliage is at its peak.

3. Fort Point Open Studios
Friday, October 14th (4:00 PM – 7:00 PM)
Saturday, October 15th & Sunday, October 16th (12:00 PM – 6:00 PM) 

In Fort Point, former warehouses have become a vibrant haven for artists. Every October members of the Fort Point Arts Community host Fort Point Open Studios where guests are invited to come tour their studios and view their work. You can chat with the artists and browse their pieces, most of which are available for purchase. This year the Fall Open Studios take place from October 14 – October 16 with an evening kick-off on Friday night. If you're looking to bring home an authentic piece of artwork created here in Boston, this is the place to go!


4. Take a cooking class
A cooking class is a great way to mix and mingle with local Bostonians and learn something new in the process. We love classes at Stir in the South End (although classes tend to book quickly) and the BCAE (Boston Center for Adult Education). On their fall roster the BCAE has classes like “Hand Pies, Flatbreads & Pizza,” “Fall Risottos,” “Cooking with Wine: Fall Edition,” and “Cheese Making Workshop." Register online at  

5. Support local artists and makers at SoWa Sunday.
The SoWa Open Market is a combination of artist market, vintage market, farmers market and food trucks. With everything in one place, it’s a popular destination every Sunday, where it runs from 10:00 AM – 4:00 PM. Browse handmade wares from local artisans, pick up some produce from the farmers market and then re-fuel with lunch at the food trucks and a beverage in the beer & wine garden! SoWa runs through Sunday, October 30th and there’s typically a special Halloween edition of the market to celebrate the last weekend!

6. Treat yourself to a pastry at Mike’s or Modern Pastry in the North End.
No trip to Boston is complete without a pastry from one of these two North End establishments! Mike’s Pastry seems to be favored by Boston guidebooks, but in our opinion, Modern Pastry matches their quality (and usually has less of a wait). We love their cannolis and the lobster tails are stellar too! 

7. Harpoon Octoberfest
Friday, September 30th (5:30 PM - 11:00 PM)
Saturday, October 3 (1:00 PM - 7:00 PM)

Harpoon’s annual Octoberfest is a favorite among Bostonians! The festival has been happening since 1990 and has become a tradition that everyone looks forward to. This year it falls on Friday, September 30th and Saturday, October 3rd. At Oktoberfest guests taste Harpoon brews, enjoy oompah bands, German food and games.

8. Take a Ghost Tour
A ghost tour is the perfect way to learn about the haunted history of the city. Haunted Boston (by foot) and Ghosts & Gravestones (by trolley with some walking) are both great options. Ghost Tours fill especially quickly for the month of October, so it’s wise to make reservations well in advance. 


9. Day Trip to Salem, MA

The place to be in the month of October is Salem, Massachusetts. Known for the Salem Witch Trials in 1692, many tourists are drawn to the spooky destination around Halloween. We recommend a visit to the Burying Point Cemetary, a tour of the Witch House, and a night time ghost tour. Also be sure to stock up on candies from the the Ye Olde Pepper Companie, the oldest candy company in the United States. For more ideas of what to do in Salem, check out our sample itinerary for a day trip. To get to Salem you can take the Rockport/Newburyport commuter rail train from North Station or rent a Zipcar.

10. Enjoy a Show in the Theater District

Boston has a wonderful arts scene and has plenty to offer when it comes to theater. Boston's Theater District houses many venues, like the Boston Opera House, Wang Theater, Shubert Theater, Wilbur Theater and more. In the fall you can catch "An American in Paris" on stage at the Wang Theater or comedians like Jim Gaffigan and Marc Maron performing at the Wilbur. Blue Man Group, a perennial favorite, runs shows weekly at the Charles Playhouse throughout the year. If music more your scene, you can also catch a concert at the Blue Hills Bank Paviliion ro the House of Blues.

11. Stroll Historic Beacon Hill

The charming neighborhood of Beacon Hill has even more ambience in the fall. The historic neighborhood is filled classic brownstone homes and bumpy cobblestone sidewalks. Beacon Hill takes Halloween seriously and if you're here in the month of October, you're bound to see some unique decorations and displays. After sightseeing, stop in to Tatte, a local bakery on Charles Street for a confection and a latte.

12. Treat Yourself to Brunch at Mistral

Mistral in Boston's South End offers one of the best brunches in the city and gets rave reviews. We're fans of their Valhrona Hot Chocolate, served with a handcrafted marshmellow and the Graham Cracker Crusted Challah French Toast. Enjoying a meal in their French-inspired dining room is a treat that shouldn't be missed! Mistral's Brunch is offered every Sunday from 10:30 AM - 2:00 PM, and we recommend making a reservation in advance.


13. Hop on a Hubway Bike

Another great way to see the city is by bike! Hubway is a bicycle sharing program and you'll see their bike stations at public places across the city. The two stations closest to the Inn are the station by the Public Garden, at the corner of Boylston Street and Arlington Street, and by the Transportation Building on the corner of Stuart Street and Charles Street. Purchase your pass from any Hubway station kiosk, unlock a bike and you'll be ready to ride! Once you're finished, you can return your bike to any station. A 24 hour pass costs just $6. (As a tip, riders will want to note that bikes are not permitted in the Public Garden).

14. Shop the Copley Square Farmers Market

The Copley Square Farmers Market is a seasonal market held in Copley Square every Tuesday and Friday (through mid-November). You can find local herbs, produce, baked good, flowers and more at the market from providers like Siena Farms. Just a short walk from the Inn, it's a great place to stock up on groceries for your stay. With a full kitchenette in every room, you can take advantage of cooking and enjoying meals in your suite.  

15. Pumpkin Festival on the Common
Sunday, October 23

If you're looking for a family friendly Halloween activity, we recommend the Pumpkin Festival held by the Frog Pond on the Boston Common. Kids can bring a carved and hollowed out jack-o-lantern with them and it will be lit and floated on the pond. At the event they can decorate a luminary to be displayed around the Frog Pond, join in the costume party, and enjoy stories, treats and drinks.

16. Shop on Newbury Street

The best shopping in Boston can be found on Newbury Street in the Back Bay. Newbury Street stretches for eight blocks and has everything from high end boutiques to large chain retailers, along with plenty of salons and dining options. Newbury Street is just around the corner from the Inn so you won’t have to carry your shopping bags very far!


17. Cozy up in a cafe

There's no shortage of beautiful cafes in Boston, but our recommendations for fall include Jaho and Ogawa. Jaho has two locations in the city, but we especially love the newest location on Washington Street in Downtown Crossing. The location doubles as coffee shop and wine bar and the sleek space is a great spot to enjoy either type of beverage. Ogawa Coffee gets our recommendation specifically for their incredible latte art. Request something seasonal, like a pumpkin or a ghost! There's truly nothing better than cozying up with a warm drink when the days get colder.

18. Visit a Museum

No trip to Boston would be complete without a museum visit! The difficult part will be choosing which you'd like to visit most. The largest and one of the most popular is the Museum of Fine Arts, which houses everything over 500,000 works of art and welcomes over a million visitors each year. For contemporary art, the ICA (Institute of Contemporary Art) in the Seaport district is the place to go. Other options include the Museum of Science, the Boston Children's Museum, Harvard Museum of Natural History and the Isabella Stewart Gardner Museum.

19. Picnic along the Esplanade

On a nice day, one of our favorite ways to enjoy the city is to pack a picnic. Half of the fun is piecing together a meal from shops in the neighborhood. Pick up meats and cheeses from Formaggio, baked goods from The Buttery, and a bottle of wine from Urban Grape - all in the South End! You can picnic in any park, but we think the trip over to the Esplanade is worth it for a beautiful view of the Charles River. Grab a spot on one of the docks and enjoy your picnic with a side of people watching.   

20. Go Apple Picking

It wouldn't be fall in New England without a trip to an orchard. There are a number of farms nearby, and pick-your-own apples are worth a trip out of the city. Farms like Belkin Family Lookout Farm, Boston Hill Farm, and Honeypott Hill are about an hour outside of the city and offer an idyllic experience. Fill a bag of apples and enjoy other orchard treats like apple cider and cider donuts!

We hope this list of the best fall activities in Boston helps you with your trip planning! If you have any questions or would like to book a stay at the Inn at St. Botolph, please contact us at 617.236.8099.

Topics: Recommended Activies

The Inn at St. Botolph

Live like a local in a historic Boston brownstone.

The Inn @ St Botolph is Boston’s affordable luxury hotel. Situated in the prominent Back Bay neighborhood it offers understated contemporary interiors graced with traditional styling and comfort. It’s the perfect destination for professionals on extended stay or families desiring the intimacy of a private residence dressed up with refreshingly customized services.

 The Inn @ St Botolph offers affordable luxury with edited services.

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  • Video intercom to talk to visitors at the front door
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