Summary

• Experience the charm of Massachusetts fall with activities like apple picking, hiking, and visiting Salem during the Halloween season. It's the perfect time to embrace traditions and enjoy stunning foliage.
• Explore Massachusetts orchards like Honey Pot Hill Orchard and Shelburne Farm for a fun-filled day of apple picking, hayrides, and corn mazes. You'll leave with bags full of tasty apples and wonderful memories.
• Take advantage of the vibrant fall foliage by hiking the scenic trails of the Berkshires, including Mount Greylock and Bash Bish Falls. Enjoy the breathtaking views of red, orange, and yellow leaves and immerse yourself in the beauty of nature.

When autumn arrives in Massachusetts, it brings a bounty of quintessential New England activities and sights. From apple picking at the state's many orchards to leaf peeping along stunning drives, there are myriad ways to embrace the fall. One classic autumnal activity is visiting Salem in October when the city goes all out celebrating Halloween with its month-long Haunted Happenings festival. The spectacular foliage also draws people to Massachusetts for hiking and outdoor activities in places like the Berkshires, where the mountain trails treat you to red and orange vistas. Fall is also an ideal time to tour historic homes dressed up in period splendor and to shop at farmer's markets overflowing with seasonal produce. Outdoor fall festivities like hayrides, corn mazes, and pumpkin festivals make for old-fashioned fun. And sports fans will want to catch the Head of the Charles Regatta where rowers race along the Charles River in Cambridge. With so many ways to soak up fall in Massachusetts, it's easy to see why it's one of the best times of year to visit.

RELATED: The 10 Best Places To Visit in Massachusetts For the Best Leaf Peeping

This article provides valuable insights into the beauty and charm of the Massachusetts fall season. It references hotels with ratings of 8.2 or higher from Kayak.com at the time of publication for potential travel inspiration. Please be aware that hotel ratings can change, and the accuracy and availability of information may vary over time. Readers are strongly encouraged to independently verify all details, including accommodations and activities, before making any travel plans, as ratings and availability may change over time. Travel arrangements should be made based on the most up-to-date and accurate information to ensure a smooth and enjoyable trip.

Go Apple Picking

Autumn brings apple picking season to Massachusetts, where families can visit the numerous orchards and farms perfect for picking your own fruit. Popular spots like Honey Pot Hill Orchard, Carlson Orchards, and Shelburne Farm let you select apples straight from the tree. Kids will love roaming the orchards, searching for the perfect apple, while adults can sample fresh cider and baked goods. Orchards also have other fall activities like hayrides and corn mazes. With so many places across Massachusetts offering pick-your-own-apples and more, autumn is the ideal time to embrace this beloved fall tradition. Visitors will leave with bags full of tasty apples and memories of a delightful day at the orchard.

• Honey Pot Hill Orchard (Stow) - $22 per half-peck bag
• Shelburne Farm and Stables (Stow) - $20 for a 10lb bag, $15 for a half peck bag
• Tougas Family Farm (Northborough) - $19 for a half peck bag, $29 for a full peck bag

Hike The Trails To See The Foliage

One of the best ways to experience the stunning fall foliage in Massachusetts is by hiking trails like those in the Berkshires. The autumn colors in this region create spectacular views. Top hiking spots to take in the vibrant red, orange, and yellow leaves include Mount Greylock, the highest peak in Massachusetts. The Holyoke Range in the Connecticut River Valley also offers marvelous vistas. And the trails to Bash Bish Falls wind through forests ablaze with color. The fall scenery along these hikes and others across Massachusetts make them hugely popular during foliage season. Put on your hiking boots and breathe in the crisp autumn air as you trek through a landscape transformed by the turning leaves.

- Peak foliage season is usually mid-October in most parts of Massachusetts. Keep an eye on foliage reports to know when colors are at their best.

- Head to Western MA. Areas like the Berkshires tend to have more varied elevations and mixed forests, creating a vibrant display of color. Popular hikes include Mount Greylock, Bash Bish Falls, and the Appalachian Trail.

- Many of the state parks have great hiking trails with excellent foliage viewing like Wahconah Falls State Park, Mt. Tom State Reservation, and Mohawk Trail State Forest.

- Go to lesser-used trails. Popular hikes can get crowded during peak season. Find more seclusion on trails like Lathrop Trail, Chesterfield Gorge, or Prospect Rock.

Visit Salem During Halloween Season

For a festive and spooky way to celebrate autumn, visit Salem, Massachusetts, during October, when the city embraces its witchy history. The month-long Haunted Happenings festival fills October with parades, shows, tours, and more that honor Salem's link to the infamous witch trials. Tour the Salem Witch Museum to learn this fascinating history and visit memorials for the victims. Also join a guided walk to learn about the city's haunted past. Or check out the variety of psychic and magic shops clustered in the city center. With its witchy vibe and celebrations, Salem is the perfect place to get into the Halloween spirit each fall. The huge crowds flocking here each October attest to its popularity during the creepiest time of year.

• Haunted Happenings
• The Salem Psychic Fair and Witches’ Market
• The Official Salem Witches' Halloween Ball

RELATED: 10 Quirky Roadside Attractions in Massachusetts Worth A Road Trip

Have A Fall Feast With Local Ingredients

Autumn in Massachusetts brings a bounty of seasonal ingredients perfect for making hearty fall meals. From apples to cranberries to squash, the state's local farms and markets overflow with produce. Visitors can take advantage of dining at restaurants crafting menus around the pumpkin, sweet potatoes, Brussels sprouts, and other fall favorites. For the ultimate Massachusetts experience, find eateries featuring local specialties like cranberries, apple cider, and pumpkin pie. The North End in Boston offers delicious fall Italian cuisine. And many farm-to-table restaurants in western Massachusetts serve freshly picked produce. With so many delicious local ingredients, autumn is a great time for visitors to enjoy the flavors of the season by dining out at Massachusetts restaurants.

Visit Kimball Farm (Westford, MA)

They are famous for their fresh homemade apple cider donuts and hot apple cider. Their pumpkin pie is freshly baked with a flaky crust.

RELATED: 10 Comfy Cafes That Make You Feel At Home In Salem, Massachusetts

Go Leaf Peeping On A Scenic Drive

One relaxing way to revel in Massachusetts' fall foliage is by taking a scenic autumn drive. Popular routes like the Mohawk Trail in the western part of the state or the artery from Boston to the Berkshires offer stunning vistas of ripe fall colors. Driving allows you to cover more ground than hiking and take in expansive views of blazing reds, oranges, and yellows across hillsides and valleys. Stop at farm stands along the way for fresh apple cider and pumpkin donuts. Pull over at scenic overlooks and snap photos of the brilliant foliage. Or stop to stroll short nature paths. While hiking immerses you directly in the foliage, a drive lets you witness Mother Nature's artistry from magical perspectives only accessible by car.

Here are some of the best driving routes for leaf peeping in Massachusetts:

• Mohawk Trail (Route 2) - This iconic scenic byway in the Berkshires is considered one of the best leaf-peeping drives in the country. Travelers get breathtaking views of autumn color alongside rivers, farms, and forests.
• Jacob's Ladder Trail - For a truly stunning and secluded fall drive, this winding country road through the Berkshires is hard to beat. It's less traveled than some other routes and offers gorgeous vistas.
• Blue Hills Parkway (Route 138) - Close to Boston, this drive lets visitors become immersed in brilliant red maple leaves contrasted against the Blue Hills. The route goes through a state park and offers many great outdoor recreation opportunities.

Tour Historic Homes Led By Guides In Period Dress

For a unique way to learn about history, visitors can tour Massachusetts' historic homes during fall events when guides wear elaborate period costumes. Properties managed by organizations like The Trustees offer special tours where the guides dress in custom-made colonial-era clothing, transporting visitors back in time. Female guides wear long dresses with corsets, while men don breeches and waistcoats. Intricate details like bonnets and buckled shoes further immerse visitors in the past. Guests can chat with these engaging, costumed guides to hear tales of previous eras delivered with drama and wit. From pilgrims to Victorian aristocrats, the carefully crafted period dress worn by the guides connects visitors intimately with the lives of those who came before. It's an eye-opening and enjoyable way to discover history this fall.

Here are 3 tours of historic homes led by guides in period dress in Massachusetts:

• The Trustees - Various historic property tours, including Naumkeag in Stockbridge, Ashely House in Deerfield, and Castle Hill on the Crane Estate in Ipswich. Guides wear clothing replicating the era.
• Historic Deerfield - Take a guided tour of 12 authentically restored 18th and 19th-century homes with interpreters dressed in period clothing.
• Gore Place - Located in Waltham, tours are led through the historic 1806 mansion by knowledgeable guides dressed in Federal-era costumes.

Attend A Fall Festival

Attending a fall festival is a beloved autumn tradition for everyone in Massachusetts. Towns across the state host lively harvest festivals in September and October, like the major Franklin Park Pumpkin Festival. These seasonal fairs feature amusement rides, carnival games, live music, food trucks with autumn eats, pie contests, scarecrow displays, and more. Kids will love activities like pumpkin painting, while adults can browse farm stands to pick the perfect pumpkin for carving. As the leaves change and the air turns crisp, fall festivals provide an ideal outdoor activity whether you're looking for family fun, a cute date, or just a festive solo outing. Visitors can sample apple cider donuts, get lost in a corn maze, and celebrate the season at these classic New England community gatherings.

These festivals capture the fall harvest season leading into Halloween and Thanksgiving in Massachusetts.

• Topsfield Fair - Topsfield October 7-16, 2023
• Franklin County PumpkinFest - Greenfield October 14-16, 2023
• Witchcraft's Wellesley Parade & Festival - Wellesley October 29, 2023
• Berkshire Cider Festival - Richmond November 5, 2023
• Haunted Happenings Grand Parade - Salem (October 28, 2023)
• Bay State Pumpkin Festival - Boston (October 28, 2023)
• Plymouth Thanksgiving Parade (November 23, 2023)

Go On A Hayride

A classic fall activity in Massachusetts is going on a hayride at one of the many farms or orchards that host them. Families, couples, and friends can snuggle up together on these rides and take in gorgeous autumn scenery. Locations like Carlson Orchards, Shelburne Farm, and Honey Pot Hill Orchard offer hayrides that tour their picturesque grounds during peak foliage season. Riders may need to bundle up in cozy scarves and blankets as the hayrides traverse hills and valleys of vibrant fall colors. After an invigorating ride, passengers can warm up with a cup of hot cider or cocoa. With stunning views and old-fashioned fun, a hayride is a wonderful way to revel in the crisp fall weather and brilliant colors of autumn in Massachusetts.

• Honey Pot Hill Orchard (Stow) - Offers daytime and haunted nighttime hayrides through 110 acres of apple orchards and woods. Visitors can stop to pick apples right from the trees during the day.
• Lookout Farm (Natick) - Hayrides take visitors through fields and woods to a scenic overlook. Kids can feed animals at the farm after. They also have a haunted "Fright Night" hayride in October.
• Butler's Orchard (Germantown) - 30-minute hayrides meander through 200 acres of farmland and forest trails during the day. They also have a haunted night ride and corn maze.

See The Head Of The Charles Regatta

Each October, visitors to Massachusetts can experience a beloved fall tradition by attending the Head of the Charles Regatta in Cambridge. This major two-day rowing event takes place on the Charles River, drawing over 11,000 athletes from around the world. Highly competitive university crews compete alongside recreational rowers during the peak of autumn foliage season. Spectators can watch the races from the banks of the river or follow along on foot or bike on parallel paths. Supporters flock to the event dressed in school colors and enjoying tailgating festivities. With elite athletics and a celebratory mood, the Head of the Charles Regatta provides a lively way to soak up fall and cheer on rowers.

Spectators traveling to and from the Regatta are encouraged to use public transportation or catch a ride on one of the complimentary shuttle buses.

Shop At Farmer's Markets

Visiting a farmer's market is a fabulous fall activity for travelers in Massachusetts. Markets across the state overflow with freshly harvested produce like squash, Brussels sprouts, beets, and turnips. Shoppers can browse pumpkins and gourds for decorating, discover honey from local apiaries, and sample artisanal cheeses. Many markets feature live music and food trucks, making them a festive weekend activity. The atmosphere is lively yet low-key, providing a glimpse into local culture. Don't miss trying apple cider donuts and warm maple kettle corn. Kids will enjoy picking out caramel apples or their own tiny pie pumpkin. With so many tasty local goods straight from family farms, farmer's markets are a scrumptious way to embrace fall's harvest spirit.

• SoWa Open Market (Boston) - The largest and most diverse market in the state. You'll find an abundance of fresh fall produce, baked goods, cider, pumpkins, gourds, flowers, and specialty items.
• Cambridge Central Square Farmers Market - A vibrant, medium-sized market featuring an excellent selection of seasonal fruits, veggies, breads, meats, cheeses, and more from local farms.
• Copley Square Farmers Market (Boston) - Boston's largest producer-only market situated in a great downtown location. Loads of autumnal foods and goods like apples, squash, cranberries, maple syrup, etc.
• Amherst Farmers Market - A fantastic western MA market with over 60 vendors. Offers farm-fresh apples, pumpkins, squash, corn, cider donuts, and specialty fall items.