AUTUMN is so wonderful, but yet so fleeting. Many Bostonians choose to travel during autumn weekends while others prefer to save their vacation time and escape the city during the winter’s snowy months.  

That leads us to wonder, BostonMan, how can we make the most of our autumn weekends this year?  

There is no need for anyone to feel “stuck in the city.” One suggestion I have is to make an actual schedule of your autumn plans. I know it can sound  rather counterintuitive to have an autumn schedule per se, however it is imperative so that the fall months are not wasted.  

We tend to lose track of time from September through November as the days move so quickly and before we know it, Christmas is upon us and we are putting ornaments on trees.  

Below are nine ideas to ponder that could help you have the best autumn in Boston possible!  

  • Explore a new park. Have coffee or a picnic. The parks in Boston are gorgeous so try to view them as an urban oasis instead of a concrete jungle. 
  • Attend a September (of if we’re lucky, October) Red Sox game. There is something nostalgic about our youth when attending a baseball game. Not sure if it is the hot dogs or the popcorn, but it makes me feel like I am carefree and ten years old again. (Side note: Fossies’s tickets has some of the best tickets in the Boston area so give them a call) 
  • Go whale watching. September and October are two of the best months for whale-watching in Massachusetts, and Boston Harbor Cruises just happens to be one of the best whale-watching tours in the Bay State! Not only does an outing with Boston Harbor Cruises get you out to prime whale-watching locations with great educational info along the way, but the views of Boston’s skyline from the water while the leaves are changing are always a sight to see, too. 
  • Check out the Head of the Charles Regatta. It is one of the biggest events in Boston during the fall and the biggest rowing event in the world. Every October, thousands of rowers from across the globe converge in Boston to race down the Charles River. There are a lot of great spots to watch the Regatta including the Eliot Bridge Enclosure, Boston University Bridge, Western Avenue Bridge, or Weeks Footbridge 
  • Tours. Boston has the Duck Boat tours, numerous narrated historical tours with notable landmarks for sight-seeing. You can also scope out a Boston brewery tour and a North End/Freedom Trail contract. A lot of people tour different places and landmarks when they are on vacation so doing a tour that you have not done before in Boston will also give you “vacation vibes.” 
  • Apple picking. About as quintessentially New England as an autumn afternoon can be, apple-picking at a local orchard like Honey Pot Hill Orchards is a fantastic way to spend a fall day! Honey Pot Hill Orchards is about a 45-minute drive out of the city, giving you the perfect amount of time to decompress from the hustle and bustle before pulling in at this gorgeous orchard. Pick your own apples, visit the farm animals, take a hayride, and basically do all the fun fall farm things in just one autumn afternoon! 
  • Spa Day/Brunch. The city of Boston has multiple, top notch spas. They also have a lot of trendy, swanky brunches happening that are filled with fun and music. Grab your squad and have an amazing “Sunday Funday” in the city. 
  • Eat at new restaurants. We eat at new restaurants when we are on vacation so experiencing new cuisine will simulate the same foodie experience you get while traveling. 
  • Try some new ways to unwind and relax such as: 
    • Garden away stress. You can still have a mini garden in the autumn without having a yard. Research shows that 30 minutes of gardening boosts mood and decreases stress. 
    • Try “beditation.” This means that before you get out of bed in the morning, try a meditation app. Did you know that the words anxiety, stress, and sleep are the most searched words on any meditation app? This will set your day up with a more relaxed tone and after all, who wants to feel nervous during the summer? 
    • Bibliotherapy, hence, read a new book 
    • Create an autumn playlist of music. Remember being a teenager and listening to your favorite ‘summer songs” over and over again? Upbeat music sends you positive vibes, creates happy memories, and lets you reminisce about summers past.

AS Shakespeare once said, “Autumn’s lease hath all too short a date.” Therefore, BostonMan Readers, make the most of Autumn in the City 2023. Enjoy time with your loved ones, make memories, and of course stay happy and healthy. Before you know it, we’ll be seeing snowflakes!

As always, please reach out with any questions or comments and make sure to follow me on social media @tiffyg77 


Tiffany Giannato is a mother, fashionista, stylist, and shopping addict! Her blogs, pictorials, and fashion tips are aimed towards empowering both women and men to look and feel their best regardless of age. Her “you can be as trendy at 61 as you were at 21” mantra has taken Boston by storm! A true Italian, Tiffany believes family, love, food, and style are always the keys to happiness!