Fall in New England has a calendar all its own. Agricultural fairs return for another season, orchards move into harvest weekends, and towns across Massachusetts, Rhode Island and New Hampshire fill October with food, music, artisans and longstanding local traditions.
If you are looking for somewhere to spend a fall weekend, we gathered seven events happening around the region in October 2026. Some have been part of the New England fall calendar for generations, while others offer a reason to explore a different corner of the region.
Topsfield Fair | Topsfield, Massachusetts
October 2–12, 2026
207 Boston Street, Topsfield, MA
The Topsfield Fair opens October 2 and runs through October 12, bringing eleven days of agricultural exhibits, arena events, midway attractions, food and entertainment to Topsfield.
The 2026 schedule includes everything from horse and oxen pulling to live performances and the fair’s well-known All New England Giant Pumpkin Weigh-Off. With different programming scheduled throughout its run, the experience can look a little different depending on which day you visit.
King Richard’s Faire | Carver, Massachusetts
Weekends through October 25, 2026
235 Main Street, Carver, MA
For a very different kind of fall tradition, King Richard’s Faire transforms its Carver grounds into a Renaissance festival each weekend through October 25.
The 2026 season features live entertainment, jousting, an artisan marketplace, food and plenty happening throughout the day. It has become a distinctive part of the fall calendar in southeastern Massachusetts.
Mashpee Oktoberfest | Mashpee, Massachusetts
October 3, 2026 | 10 a.m.–4 p.m.
Mashpee Commons Village Green, Mashpee, MA
Cape Cod gets its own start to October with the annual Mashpee Oktoberfest at the Village Green at Mashpee Commons.
The October 3 event brings together arts and crafts vendors, food, live entertainment and a biergarten for a full day on the Upper Cape. It is an easy addition to an October weekend spent exploring Mashpee and the surrounding Cape communities.
Phantom Farms Fall Fest | Cumberland, Rhode Island
Saturdays and Sundays through October 25, 2026
2920 Diamond Hill Road, Cumberland, RI
At Phantom Farms, fall festivities continue every Saturday and Sunday through October 25.
Fall Fest weekends offer another way to enjoy the season while visiting the Cumberland farm. With multiple weekends on the calendar, it is also one of the more flexible options on this list if October is already filling up.
Bowen’s Wharf Seafood Festival | Newport, Rhode Island
October 17–18, 2026
Bowen’s Wharf, Newport, RI
Autumn on the Newport waterfront comes with plenty of seafood during the Bowen’s Wharf Seafood Festival.
The two-day event celebrates the harvest of the sea with seafood from neighboring restaurants and fishermen’s associations, live music and activity throughout the wharf.
It is a distinctly coastal take on the New England fall festival, trading the farm fields for one of Newport’s waterfront settings.
Deerfield Fair | Deerfield, New Hampshire
October 1–4, 2026
34 Stage Road, Deerfield, NH
The Deerfield Fair returns October 1 through October 4, continuing a New Hampshire tradition that dates back generations.
The fair combines agricultural exhibits and competitions with entertainment, rides and classic fair attractions. For anyone planning a fall drive into southern New Hampshire, it offers a chance to experience one of the region’s longstanding agricultural fair traditions.
Fall Festivals at Applecrest Farm Orchards | Hampton Falls, New Hampshire
Weekends through the end of October
133 Exeter Road, Hampton Falls, NH
Applecrest Farm Orchards has been hosting harvest festivals for decades, with its fall calendar continuing through the end of October.
Depending on the weekend, visitors can find apple picking, a corn maze, live music, tractor rides, the farm creamery and seasonal food. Because farm activities and picking conditions can change with the weather and harvest, it is a good idea to check current conditions before visiting.
Make the Most of Fall in New England
From longtime agricultural fairs to orchard weekends and waterfront festivals, there are plenty of reasons to get out and explore New England this fall. With events happening throughout October, this list is just a starting point for enjoying the season across Massachusetts, Rhode Island and New Hampshire.
If your plans include a move, Jack Conway is here to help. And if your next move takes you outside our market, our affiliation with Leading Real Estate Companies of the World® allows us to connect you with a trusted real estate professional wherever you’re headed.
Wherever your fall plans take you, we hope you enjoy the season.
Event dates, hours and programming may change. Check directly with each event before making plans.
