October in Boston 2025: Local Events, Festivals & Hidden Gems You Can’t Miss
October in Boston can tempt even the most even the most sociable to start hibernating. The days grow shorter, it’s definitely colder, and there’s a cozy pull to stay indoors with a warm drink. However… we think it’s the opposite! Fall is the perfect time to explore what your city has to offer.
At Pao, our mission is simple: help you discover the best experiences wherever you are, whether you live in the city or are just visiting. October in Boston is packed with events that bring people together, celebrate local culture, and create memories that last long after the leaves have fallen.
From arts and culture to seasonal festivals, foodie adventures, wellness meetups, and sports gatherings, our guide will help you find all the fun Boston has to offer this October!
Arts, Culture & Entertainment
October 3, 2025 • 9PM until late!
Remnant Brewing - 2 Bow Market Way
Swifties, this one’s for you! Celebrate the new album at this free party with themed drinks and music. The first 30 attendees will receive a party bag - a little bonus for showing up early to a local favorite. It’s a fun night to meet fellow fans and enjoy the relaxed, creative vibe of the brewery.
October 9, 2025 • 9PM - 2AM
Little Haiti International Cuisine, Roxbury
BOSTON HAS VIBESS is hosting an intimate after party where local creatives come together for music, drinks, and conversation. It’s a chance to see a different side of the city’s fashion scene. You’ll leave feeling inspired by the energy and stories of the people making Boston’s fashion community tick.
October 25, 2025 • 10AM - 6PM
Copley Square, Boston
Keynote speakers, author talks, and interactive panels make this festival more than just a book fair. Explore indie presses, meet local authors, and enjoy a day that celebrates ideas, reading, and community. There are plenty of spaces to linger, discover new voices, and connect with other readers in the city.
Fall Festivals & Seasonal Fun
October 3, 2025 • 4:30PM - 8:30PM
Rowes Wharf Plaza
Pumpkin decorating, glow mini golf, face painting, and an inflatable obstacle course set the scene for a fun evening outdoors. Local food trucks and craft vendors make it easy to spend a few hours wandering and tasting. This is the perfect way to spend an evening, in our opinion!
October 4, 2025 • 10AM - 6PM
The Point, Boston
Eight local bars, cider flights, and 1,000 free donuts - a playful way to explore neighborhoods and sample what small bars and breweries are offering this season. Even if you’re familiar with these streets, the festival is a new way to meet bartenders and discover hidden gems along the route.
October 4-5, 2025 • From 12PM
The Yard Charlestown
Explore 50,000 sq ft of shopping across 80+ vendors featuring vintage, Y2K, jewelry, and local brands. Beyond browsing, you can try mini golf, visit the fill-a-bag station, snag giveaways, or even get a tooth gem for a playful seasonal touch. With 21+ areas for drinks and music, the festival blends sustainable shopping with unique experiences!
October 11, 2025 • 11AM - 9PM
Short Path Distillery
Spiked cider flights, apple cocktails, live music, and food pop-ups highlight the season at this local distillery. A relaxed indoor/outdoor event perfect for an autumn afternoon. You can linger over drinks, enjoy the music, and explore the distillery’s space in a casual, friendly way.
October 18-19, 2025 • 6PM
Reggie Lewis Track & Athletic Center
This free festival features plant-based food tastings, chef demos, and national speakers alongside kids’ activities and local vendors. A celebration of Boston’s growing plant-based scene and the people behind it. It’s a place to try something new, talk to makers, and see how local food culture is evolving.
Food, Drink & Nightlife
Every Wednesday in October • 9 PM
The Anchor, 1 Shipyard Park Boston
Enjoy free movie nights on the waterfront patio. With a full bar and kitchen open until 11 PM, it’s a low-key way to spend an evening with friends or family. The atmosphere makes it easy to grab a drink, relax, and enjoy the city’s autumn views while watching a film.
October 1, 2025 • 6:30PM - 8:30PM
Trillium - Fort Point. 50 Thomson Place Boston
Try your hand at pottery while sipping local craft beer. The guided workshop is casual and fun, and you’ll leave with a handmade piece and a memory of a relaxed evening out!
October 22, 2025 • 6:30PM - 10PM
Boston Ale House,1885 Centre Street
Thirty-one TVs, raffle prizes, complimentary wings, and a chance at TD Garden Boardroom Tickets make this a must-visit for sports fans. The local bar atmosphere keeps it casual and fun, with friends, fellow fans, and good drinks all part of the experience. It’s a lively night out that combines Boston’s sports culture with the city’s love of local spots.
health & Wellness
Ritual Boston’s Wellness Social
October 4, 2025 • 9:00AM - 12:00PM
411 Dorchester Ave, Boston
Guided workouts, a run club, cold plunges, and wellness pop-ups make this a community-centered way to start the weekend. Free coffee helps keep spirits high. You can move at your own pace, meet new people, and enjoy a morning outdoors with an easygoing, friendly vibe.
October 5, 2025 • 11AM - 12:30PM
The Anchor, 1 Shipyard Park
A low-impact, high-intensity workout by the water followed by food and drink specials. A simple way to mix fitness with a casual visit to a local favorite. It’s a relaxed, approachable session for anyone curious about barre or just wanting to try something new.
October in Boston is packed with local experiences: small breweries, indie bookstores, seasonal festivals, and fitness meetups that make the city feel alive.
With The Pao App, you can discover these stories, support local businesses, and enjoy a season full of real experiences - not just what’s popular online. Grab a jacket, step outside, and see what your city has to offer this fall.
