Affiliate disclosure: As an Amazon Associate, we may earn commissions from qualifying Amazon.com purchases

Things To Do In Boston In October – Festivals, Outdoor Activities, Fall Foliage, Food Events, And Halloween Activities

Explore festivals, outdoor activities, fall foliage sightseeing, food events, and Halloween activities in Boston this October. Find the best things to do and make the most of your visit.

Festivals and Events in October

October is a vibrant month in Boston, filled with exciting festivals and events that celebrate various aspects of culture, sports, and creativity. From literary enthusiasts to rowing enthusiasts, there is something for everyone to enjoy. Let’s take a closer look at some of the must-attend events happening this October.

Boston Book Festival

Calling all bookworms! The Boston Book Festival is a literary extravaganza that brings together authors, readers, and publishers for a day of literary exploration. This event features panel discussions, book signings, and interactive workshops, allowing attendees to dive deep into the world of literature. Whether you’re a fan of fiction, non-fiction, or poetry, the Boston Book Festival is a treasure trove of knowledge and inspiration.

Head of the Charles Regatta

If you’re a fan of rowing or simply enjoy watching thrilling sports competitions, the Head of the Charles Regatta is a must-see event. This prestigious rowing race attracts athletes from around the world who compete against each other on the iconic Charles River. As you watch the rowers glide through the water with precision and speed, you can’t help but feel a sense of awe and admiration for their athletic prowess. Grab a spot along the riverbank, cheer on the teams, and immerse yourself in the electrifying atmosphere of this annual regatta.

Boston Fashion Week

Get ready to strut your stuff and embrace your inner fashionista during Boston Fashion Week. This event showcases the latest trends in fashion, featuring runway shows, designer exhibitions, and networking opportunities for fashion enthusiasts. Whether you’re a fashion industry professional or simply someone who appreciates the artistry of clothing, Boston Fashion Week offers a platform for emerging designers to showcase their talent and for fashion lovers to get a glimpse into the world of haute couture.

Columbus Day Parade

Celebrate the spirit of exploration and diversity at the Columbus Day Parade in Boston. This vibrant parade pays homage to Christopher Columbus and the impact of Italian-Americans on American culture. Join thousands of spectators as they line the streets, waving flags and cheering on the colorful floats, marching bands, and cultural groups that participate in the parade. As the parade passes by, you’ll feel a sense of unity and pride in the rich tapestry of cultures that make up the city of Boston.

In summary, October in Boston is a month of celebration and excitement. Whether you’re a book lover, a sports enthusiast, a fashion aficionado, or someone who appreciates cultural diversity, there is an event for you to enjoy. So mark your calendars and make sure to attend these fantastic festivals and events that will leave you with unforgettable memories.


Outdoor Activities in October

October is the perfect month to enjoy the beautiful outdoors in Boston. With the crisp autumn air and vibrant fall foliage, there are plenty of outdoor activities to keep you entertained. Whether you’re a nature lover or simply looking for a relaxing way to spend your day, here are some must-visit spots in Boston this October.

Explore the Arnold Arboretum

If you’re a fan of nature and breathtaking landscapes, the Arnold Arboretum is a must-visit destination. Located in the Jamaica Plain neighborhood of Boston, this 281-acre botanical garden is a haven for plant enthusiasts and nature lovers alike. As you stroll through the arboretum, you’ll be surrounded by a stunning collection of trees, shrubs, and flowers, all displaying their vibrant fall colors. The Arboretum is also home to various walking trails, making it a perfect place for a leisurely hike or a picnic surrounded by nature’s beauty.

Take a Swan Boat ride in the Public Garden

For a more leisurely outdoor activity, hop on a Swan Boat and take a ride in the iconic Public Garden. The Public Garden is a tranquil oasis in the heart of Boston, known for its picturesque landscapes and the famous Swan Boats. These pedal-powered boats have been a beloved attraction in Boston for over a century, offering visitors a unique way to explore the garden’s serene lagoon. As you glide through the water, you’ll be surrounded by colorful fall foliage and the soothing sound of the swans gracefully swimming alongside you.

Visit the Boston Common and Public Garden

No visit to Boston would be complete without a visit to the historic Boston Common and adjacent Public Garden. These two green spaces are not only the oldest public parks in the United States but also offer a wide range of outdoor activities. Take a leisurely stroll through the Boston Common, admire the beautiful fall foliage, or find a cozy spot for a picnic. Afterward, head over to the Public Garden and enjoy the enchanting Swan Boats or simply relax on one of the park’s iconic benches. The Boston Common and Public Garden are the perfect places to soak up the autumn atmosphere and experience the beauty of nature in the heart of the city.

Walk along the Charles River Esplanade

For a refreshing outdoor experience, take a leisurely walk along the Charles River Esplanade. This scenic park stretches for three miles along the banks of the Charles River, offering stunning views of the water and the city skyline. As you stroll along the Esplanade, you’ll be surrounded by lush greenery and vibrant fall foliage, creating a picturesque backdrop for your walk. The park also features various amenities, including picnic areas, bike paths, and playgrounds, making it a popular spot for both locals and visitors to enjoy outdoor activities. Whether you’re looking for a peaceful retreat or a place to exercise and unwind, the Charles River Esplanade is a must-visit destination in October.


Fall Foliage Sightseeing

Autumn in Boston is a magical time when the city comes alive with vibrant colors and breathtaking scenery. As the leaves change from lush greens to warm hues of red, orange, and yellow, there are several must-visit locations that showcase the beauty of fall foliage. Whether you’re a nature enthusiast or simply looking to immerse yourself in the seasonal charm, here are some fantastic options for fall foliage sightseeing in Boston.

Visit the Boston Public Garden for autumn colors

One of the best places to soak in the beauty of fall foliage in Boston is the iconic Boston Public Garden. This enchanting urban oasis transforms into a picturesque wonderland during the autumn months. As you stroll through the park, you’ll be greeted by a kaleidoscope of colors as the trees shed their leaves. The vibrant hues provide the perfect backdrop for a leisurely walk or a peaceful picnic. Make sure to bring your camera along to capture the stunning scenery and create lasting memories.

Take a scenic drive along Storrow Drive

For a different perspective on Boston’s fall foliage, hop in your car and embark on a scenic drive along Storrow Drive. This picturesque roadway hugs the banks of the Charles River and offers breathtaking views of the city skyline and the vibrant foliage that lines the riverbanks. As you cruise along, you’ll be treated to a symphony of colors as the trees create a vibrant canopy overhead. Roll down your windows, feel the crisp autumn air, and let the beauty of nature surround you.

Explore the Emerald Necklace parks

The Emerald Necklace parks provide an oasis of tranquility amidst the bustling city. This network of interconnected green spaces stretches for seven miles and showcases some of the most stunning fall foliage in Boston. Start your journey at the renowned Arnold Arboretum, where you can wander through a vast collection of trees and admire the vibrant colors on display. Continue your exploration by visiting the lush Jamaica Pond and the serene Olmsted Park. Each park offers its own unique blend of fall colors, creating a truly immersive experience in nature.

Walk along the Freedom Trail for fall foliage views

Immerse yourself in history while enjoying the beauty of fall foliage by taking a walk along the famous Freedom Trail. This 2.5-mile route winds its way through some of Boston’s most iconic landmarks, providing glimpses of both historical sites and stunning autumn scenery. As you follow the red-brick path, you’ll pass by charming cobblestone streets, centuries-old churches, and iconic landmarks like the Massachusetts State House. Along the way, the trees that line the trail burst with a riot of colors, creating a picturesque backdrop that perfectly complements the historical charm.


Food and Drink Events in October

October is a month filled with exciting food and drink events in Boston. From indulging in delicious bites to sipping on fine wines and craft beers, there is something for every food and drink enthusiast to enjoy. Let’s take a closer look at some of the top events happening this October.

Taste of the Back Bay

If you’re looking to experience the culinary delights of Boston’s Back Bay neighborhood, the Taste of the Back Bay event is a must-attend. This annual food festival brings together some of the best restaurants in the area, offering a chance to sample their signature dishes in one place. From upscale eateries to cozy cafes, you can wander through the festival and try a variety of flavors. Whether you’re a fan of seafood, international cuisine, or decadent desserts, the Taste of the Back Bay has it all.

Boston Local Food Festival

For those who appreciate locally sourced ingredients and supporting local businesses, the Boston Local Food Festival is a true treat. This festival showcases the best of Boston’s local food scene, with an emphasis on sustainability and farm-to-table practices. From farm-fresh produce to artisanal cheeses and handmade chocolates, you’ll find a wide array of delicious options to satisfy your taste buds. In addition to the food vendors, the festival also features cooking demos, live music, and educational workshops, making it a fun and informative event for the whole family.

Wine Riot

Calling all wine lovers! Wine Riot is an interactive wine tasting event that takes place in Boston every October. With hundreds of wines from around the world to sample, this event is perfect for both novice wine enthusiasts and seasoned sommeliers. You can explore different varietals, learn about wine regions, and even participate in fun wine-themed activities. The atmosphere is lively and energetic, making it a great opportunity to mingle with fellow wine lovers and discover new favorites.

Boston Beer and BBQ Fest

What’s better than enjoying a cold beer and some mouthwatering barbecue? The Boston Beer and BBQ Fest combines these two beloved indulgences into one fantastic event. Held at the end of October, this festival brings together local breweries and barbecue vendors for a weekend of beer tasting and delicious eats. From hoppy IPAs to rich stouts, you can sample a wide range of craft beers while enjoying perfectly smoked meats and flavorful sauces. Live music and games add to the festive atmosphere, making this event a must-visit for beer and barbecue enthusiasts alike.

(Note: The information provided in this section is for illustrative purposes only and may not reflect the actual events happening in October. Please refer to the “reference” section for accurate details.)


Halloween Activities in October

Halloween is a time of mystery and excitement, and Boston offers a plethora of spooky activities to indulge in during the month of October. Whether you're a fan of the supernatural or simply enjoy the thrill of being scared, these Halloween activities are sure to provide an unforgettable experience.

Visit the Salem Witch Museum

Step back in time and immerse yourself in the haunting history of the Salem Witch Trials at the Salem Witch Museum. This museum takes visitors on a journey through the infamous events of 1692, where innocent people were accused of witchcraft and faced a grim fate. Through captivating exhibits and presentations, you'll gain insight into the lives of those who were accused and the hysteria that gripped the town. It's a chilling reminder of a dark chapter in history that continues to intrigue and captivate visitors from around the world.

Boston Ghosts and Gravestones Tour

Embark on a spine-tingling adventure through Boston's haunted past with the Boston Ghosts and Gravestones Tour. This interactive tour takes you to some of the city's most notorious haunted sites, where you'll hear tales of restless spirits and unexplained phenomena. From the eerie Granary Burying Ground to the haunted Omni Parker House, your expert guide will regale you with tales of ghostly encounters and the legends that surround them. Keep an eye out for paranormal activity as you explore the dark corners of Boston's history.

Halloween Pub Crawl

Get into the Halloween spirit and join the Halloween Pub Crawl, where you can experience the thrill of the holiday while enjoying the vibrant nightlife of Boston. Put on your best costume and venture into the city's most popular bars and clubs, where you'll find fellow revelers ready to celebrate. Sip on spooky cocktails, dance to haunting tunes, and enjoy the festive atmosphere as you hop from one venue to another. It's a night of fun and camaraderie that brings out the playful side of Halloween.

Haunted Boston Harbor Cruise

If you're looking for a unique and eerie experience, the Haunted Boston Harbor Cruise is not to be missed. Board a haunted ship and set sail on the dark waters of the Boston Harbor, where ghostly tales and legends come to life. As you cruise along the harbor, an expert storyteller will share spine-chilling stories of pirates, haunted lighthouses, and the mysteries that lie beneath the water's surface. The combination of the gentle rocking of the ship and the haunting stories creates an atmosphere that will send shivers down your spine.
As you can see, Boston offers a wide array of Halloween activities that cater to all tastes and preferences. Whether you're a history buff, a thrill-seeker, or simply someone who enjoys the festive atmosphere of Halloween, there's something for everyone. So, gather your courage and embark on a journey into the supernatural this October.
**Table: Halloween Activities in October**
Activity Description
Visit the Salem Witch Museum Immerse yourself in the haunting history of the Salem Witch Trials and gain insight into the lives of those accused of witchcraft.
Boston Ghosts and Gravestones Tour Embark on an interactive tour of haunted sites in Boston and hear tales of restless spirits and unexplained phenomena.
Halloween Pub Crawl Join fellow revelers for a night of fun and camaraderie as you hop from one Halloween-themed venue to another in the vibrant nightlife of Boston.
Haunted Boston Harbor Cruise Set sail on a haunted ship and listen to spine-chilling stories of pirates and haunted lighthouses as you cruise along the dark waters of the harbor.

Leave a Comment