October in Boston: Travel Inspo for Michelle and Mitch’s Wedding

Hello friends and family of the bride and groom! In the lead up to Michelle and Mitch’s big day, many of you will be visiting Boston from out of town. They picked an incredible time to get married- late October is the peak of Boston’s autumn foliage, and the city will be alive with all things festively fall. Here’s a quick reference guide for your visit:

Boston Hotels

Information for discounted rates at The Newbury is found on the wedding website. If you’d like to stay at a different hotel, Cassidy can research the options which best align with your criteria and book your choice- for free!

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Things to do

To save you time, we’ve selected the best tours and activities. You’ll find everything from food tours to harbor cruises, and a number of quirky options- there’s something for everyone on this list!

Browse tours and activities
 
Boston Sightseeing
Personalized Google Map List
Around the City
  • Freedom Trail: A 2.5-mile walking route that connects 16 historic sites like Paul Revere’s House, Boston Common, and Faneuil Hall.
  • USS Constitution: The world’s oldest commissioned warship still afloat; now a museum
  • Boston Common & Public Garden: A large public park (fun fact: it’s the oldest city park in the US)
  • Fenway Park: Boston’s famous baseball stadium. Even if the Red Sox aren’t playing, you can tour the stadium’s interior.
  • Quincy Market / Faneuil Hall: Great for food, local shopping, and people-watching.
Museums & Culture
  • Museum of Fine Arts: Excellent collections, and a cozy indoor activity if the weather’s chilly.
  • Isabella Stewart Gardner Museum: Venetian-Gothic architecture and a mysterious art heist story make it extra intriguing.
  • Boston Tea Party Ships & Museum: An Interactive and fun take on the typical museum experience- expect some performative flair with a solid dose of historical facts
  • Student-Led Tour of Harvard: See the famous university campus and hear about studying there from a student first-hand- no minimum GPA required to join the tour 😉
Top Spots for Leaf Peeping In Boston (No Car Needed)
  • Boston Public Garden & Boston Common
  • Charles River Esplanade
  • Arnold Arboretum (Jamaica Plain)
  • Beacon Hill
Seasonal Shoutouts
  • Salem, MA (Day Trip): Just 40 minutes away—October is prime time to explore its witch trial history, haunted happenings, and costume-filled streets. You can get an Uber or rent a car, or take the ferry there
  • Ghost Tours: Boston offers nighttime ghost tours through historic (and reportedly haunted) spots
  • Apple Cider Donuts & Pumpkin Treats: Try Blackbird Doughnuts, Flour Bakery, or local farmers markets.
  • Newbury Street: Great for shopping with foliage and fall-decorated storefronts.

 

Additional Travel Support

If you’re thinking about making a larger trip out of Michelle and Mitch’s wedding weekend, here are some ideas. Please reach out to Cassidy for FREE itinerary information and FREE hotel booking for these or any other destinations:

Vermont or New Hampshire (Road Trip, 2–4 hours north)
  • Why go: It’s still possible to see some good fall foliage in Southern Vermont, and fall is a nice time to meander through the charming small towns, covered bridges, cider mills. Vermont is known for lots of artisanal products: cheeses, ciders, dairy products as well as apple cider and maple syrup.
  • Highlights: Stowe, Woodstock (VT); White Mountains, Franconia Notch (NH).
  • Ideal for: Scenic drives, hikes, cozy inns.
New York City (Train or bus, ~4 hours from Boston)
  • Why go: Iconic city energy, Central Park in fall is stunning.
  • Highlights: Museums, Broadway, rooftop views, diverse neighborhoods.
  • Tip: Acela train from Boston is fast and scenic.
Hudson Valley, NY (Car, ~3.5 hours from Boston, ~2 hours from NYC)
  • Why go: Beautiful countryside, farm-to-table food, vineyards, art galleries.
  • Highlights: Storm King Art Center, small towns like Beacon and Rhinebeck, fall foliage.
  • Great for: A slower pace after the city, especially for food/wine lovers.
Washington, D.C. (Train from NYC ~4 hours or Boston ~1.5 hour flight)
  • Why go: National monuments + world-class museums, many of which are free.
  • Highlights: National Mall, Smithsonian, Georgetown.
  • Bonus: Still mild weather in late October, with fall color starting to show.
Acadia National Park, Maine (5–6 hours drive from Boston)
  • Why go: Dramatic coastal views, cliffs, forests, lobster towns.
  • Highlights: Cadillac Mountain sunrise, Bar Harbor, hiking trails.
  • Good to know: Late October is just before many coastal towns start closing for the season—quiet but still beautiful. It will be colder though, so be sure you have warm clothes if you want to head this way.
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