We help people live and invest better, and today we're leaning into the living better half of our mantra. This means enjoying every season to the fullest. And if you're in Boston this fall, you’re in for a real treat. Whether you're a local or just visiting, or looking to settle down and rent or buy your dream home: let’s talk about how you can live better this season with the best fall activities the city has to offer.

Here’s the thing: Boston in the fall? It’s iconic. People travel from all over the world to experience Autumn in New England. Think foliage that’ll stop you in your tracks, food that screams comfort, and events that turn a good day into a great one. Let's get right into our top ten fall to-do's! 

1. Stroll Through the Boston Common and Public Garden

Start your fall off right with a walk through Boston’s oldest—and dare I say—most beautiful parks. The trees are going to be absolutely on fire with color. This is where Boston shows off. And the Swan Boats? They’re not here forever, so you’ve got to catch them before they pack up for the season.

• Pro Tip: Early mornings, a coffee in hand, and a casual stroll = peak Boston. Take it in while you can! 

2. Leaf Peeping at the Arnold Arboretum

We’re talking 281 acres of leaf-peeping magic. The Arnold Arboretum is a must for fall foliage. You don’t need to escape to the mountains to feel like you’re in a fall postcard.

• Best Time: Mid-October to early November, when the colors are pure fire. Free guided tours? Yep. Just another reason to put this on your list.

3. The Head of the Charles Regatta

Now, here’s where the energy really ramps up. Boston is known for its tradition, and this regatta? It’s as Boston as it gets. Since 1965, the Head of the Charles Regatta has brought thousands of rowers to the Charles River to compete in the world's largest 3-day regatta. You’ll have rowers from all over the world competing, and the Charles River is the place to be for two days of non-stop action.

• Dates: October 18-20, 2024.
• Where to Watch: Eliot Bridge is a hotspot, but if you want to escape the crowds and still catch the excitement, head over to the Harvard side. Cambridge is gorgeous.

4. Haunted Boston: Ghost Tours

You know Boston’s history runs deep, and with that comes its spooky side. If you’re into haunted tales and eerie vibes, the city’s ghost tours will not disappoint. You’ll walk through historic neighborhoods, learning about the dark, haunted side of Boston that’s been around for centuries.

• Tours to Book: Ghosts and Gravestones or Haunted Boston Ghost Tours. If you prefer to take it in while sitting down, the Boston Trolley Tours are a great way to get spooked without getting 5K steps in. 

5. Boston’s Farmers Markets: Fall Edition

Pumpkins. Apples. Cider doughnuts. You know what time it is. The farmers markets in Boston are on another level in the fall. It’s fresh, it’s local, and it’s everything you want from a fall day.

• Top Markets: Copley Square Farmers Market, Boston Public Market, SoWa Open Market.
• Fall Vibe: SoWa Spooktacular (October 27, 2024). If you haven’t been to SoWa in the fall, you’re missing out. Think local artists, food trucks, and a Halloween festival to top it off.

6. Day Trip to Salem: The Halloween Capital

Listen, if you want to experience Halloween to its fullest, Salem is a must. It’s a short train ride away, but it feels like stepping into an entirely different world. Salem's Haunted Happenings can get pretty crowded the closer it gets to halloween, so the earlier in the season you can make it out, the better. Witch history, haunted happenings, and more events than you can fit into a day.

• Best Time to Go: October weekends are packed, but if you want to skip the massive crowds, go midweek. 
• Salem Highlights: The Witch Museum, Witch House, and evening walking tours that’ll give you chills. Just trust me—you’ll feel the Halloween spirit.

7. Apple Picking and Fall Festivals

Is it even fall if you haven’t gone apple picking? I don't think so. Boston’s just a stone’s throw from some of the best orchards in New England. Pick apples, grab a hayride, and don’t leave without a bag of cider doughnuts.

• Top Spots Near Boston: Honey Pot Hill Orchards, Lookout Farm, Cider Hill Farm.
• Pro Tip: Get your pumpkins, apple cider, and donuts while you’re at it. Make it a full fall day.

8. Indulge in Fall’s Best Eats

Fall flavors are in full swing, and if you’re not treating yourself, you should be. From pumpkin lattes to hearty comfort food, Boston’s restaurant scene delivers.

• Must-Try Spots: Tatte Bakery for pumpkin spice everything, Kane's Donuts for apple cider doughnuts, and Dig Inn for seasonal bowls that taste like fall in a dish.

9. Fall Festivals and Events

Boston’s festival scene is strong, especially in the fall. Whether you're into books, food, or culture, the city’s got something for you.

• Boston Book Festival: October 14-15, 2024, in Copley Square. It’s not just about books; it’s about the experience—meeting authors, hearing their stories, and getting inspired.
• Indigenous Peoples Day: October 14, 2024, at Boston Common. Cultural performances, food, and a celebration of history and community.

Ready to Live Better in Boston?

Boston in the fall is an experience you don’t want to miss. It’s vibrant, it’s alive, and it’s the perfect time to explore everything the city has to offer. Whether you’re leaf-peeping, picking apples, or diving into the city’s haunted history, this is your season to live better in Boston. And if you're looking to take that next step—whether it’s developing, buying, renting, or selling in Boston—CHARLESGATE is here to guide you every step of the way. With our full-service approach to real estate, we don’t just help you find a place to live—we help you invest in the lifestyle and future that Boston has to offer.