There’s no season more magical in New England than autumn; crisp air, blazing foliage, and towns alive with a renewed energy to harvest and hunker down for the winter ahead. If you’re looking for a fall escape that blends train travel, charming communities, and festival vibes, ride the Amtrak Downeaster and hop off into some of the best autumn celebrations the region has to offer.

We've highlighted some of our favorite fall festivals that bring their own flavor to the season. Best part? You can take the Downeaster and find yourself just steps from these local events.

1. Powder Keg Beer & Chili Festival (Exeter, NH)

• When: Saturday, October 4, 2025, 12:00–4:00 p.m.

• Where: Swasey Park, Downtown Exeter

• What to Expect:

  • A gathering of breweries bringing beer of all styles to sample.

  • A chili competition where attendees can taste and vote for favorites.

  • Live entertainment, family-friendly programming, and a festive autumn ambiance.

  • VIP and general admission ticket options; “chili-only” tickets for designated drivers or non-drinkers.

  • Check it out here!

2. Freeport Fall Festival (Freeport, ME)

• When: October 3-5, 2025

• Where: Freeport, Maine

• What to Expect:

  • Hundreds of vendors featuring artisan goods, fall treats, and local food.

  • Live music, family-friendly events, and lots of “shop + stroll” moments.

  • Seasonal specials at Freeport’s famous outlets, charming streets, and cozy cafés.

  • Access: The Downeaster stops in Freeport, with the platform just steps from Main St. Make this festival a centerpiece of a day trip or overnight stay.

  • Learn more today!

Why the Downeaster is the Perfect Way to Explore & Enjoy Fall in New England

The train route weaves through scenic New England and connects you to festival towns without the stress of driving.

Oversized windows and relaxed seating make it ideal for catching vibrant fall colors as you travel.

Enjoy onboard amenities such as the Cafe and sip and snack as you please - we will take care of the rest!