The Ultimate Fall Festivals: Things to Do Around Boston This Fall

Fall in Boston is a magical time when the air turns crisp, leaves turn vibrant shades of orange and gold, and festivals pop up all around the region. Whether you’re a fan of classic country fairs, medieval revelry, or spooky Halloween attractions, there’s something for everyone to enjoy. Here’s a look at the best fall festivals and seasonal activities around Boston, including how to plan the perfect autumn weekend.

Which Fall Festival Around Boston is Your Favorite?

Boston is known for its incredible variety of fall festivals, with two of the most popular being the Topsfield Fair and King Richard's Faire.

The Topsfield Fair, America’s oldest fair, holds a special place in many hearts. It offers a nostalgic blend of agricultural exhibits, live music, and carnival rides. My personal favorite? The giant pumpkin weigh-off! Watching those massive gourds tip the scales never gets old. If you're a fan of classic Americana with a fun twist, the Topsfield Fair is hard to beat.

However, King Richard’s Faire offers something completely different—an immersive, medieval experience. It’s not just a fair; it’s like stepping back in time with jousting tournaments, sword-swallowing performances, and artisans showcasing their crafts. If you’re fascinated by history or just love unique experiences, this is the festival for you.

The Ideal Fall Weekend Itinerary Around Boston

Planning the perfect fall weekend in Boston? Balance is key. You can pack a lot into two days without feeling rushed by mixing festival fun, outdoor activities, and seasonal events.

Saturday: Start your weekend with a morning hike at Blue Hills Reservation or a walk along the Charles River Esplanade to soak in the stunning foliage. Then, head to the Topsfield Fair in the afternoon. Be sure to explore the agricultural exhibits and grab some fried dough for a classic fair treat. Stick around for the evening fireworks or a concert to end the night with a bang.

Sunday: Step into another world at King Richard’s Faire in Carver, MA. Spend the day exploring the fantasy-themed village, cheering for knights in armor, and indulging in a turkey leg. Don’t miss the lively performances, from fire eaters to jesters. After the Faire, end your weekend with a haunted hayride at Barrett’s Haunted Mansion or Factory of Terror for some spooky, adrenaline-pumping fun.

Must-See Attractions at the Topsfield Fair

The Topsfield Fair has so much to offer, it can be overwhelming. Here’s how to plan your visit to make the most of it:

• Giant Pumpkin Contest: The highlight of the fair! You won't believe the size of these pumpkins.
• Agricultural Exhibits: Get a taste of rural New England by checking out livestock, produce, and flower displays.
• Midway Rides & Games: Fun for all ages, the Midway offers thrilling rides and carnival games that will keep you entertained for hours.
• Food: You can’t leave without sampling some fair classics—fried dough, candy apples, and local seafood.

King Richard’s Faire: A Medieval Escape

There’s nothing quite like King Richard’s Faire, where you can dive into medieval life. The 80-acre wooded village is full of lively characters, from knights to wenches, and performances that make you feel like you’re part of the action.

My favorite activities? Watching the live jousting tournaments and browsing the artisan booths, where you can find handmade swords, leatherwork, and costumes. The fantasy world created here is a refreshing break from the everyday, and the interactions with actors in full character make the experience truly immersive.

Haunted Hayrides and Spooky Attractions

Boston’s fall wouldn’t be complete without some spooky thrills. Haunted hayrides and Halloween attractions here are top-notch compared to other regions because of their rich history and attention to detail. From the Spooky World at Mel’s Funway Park to the haunted corn mazes in nearby towns, each experience has its own unique, chilling twist. What sets Boston’s haunted attractions apart is the eerie backdrop of old colonial towns, adding an authentic, historic creepiness that you won’t find anywhere else.

This fall, make the most of Boston’s festivals, fairs, and haunted happenings, and experience all the magic the season has to offer!