JP Dog Parade

This year’s event will take place on Saturday, October 25, 2025, and will feature a parade down Centre Street with music from JP Honk and a police escort. The parade culminates in a red carpet walk at Loring Greenough House, with judging and prizes awarded for the best costume. Join us for Jamaica Plain's premier event - the Canine Costume Parade! The parade starts at the First Baptist Church and finishes at the Loring Greenough House with a fashion show and judging by celebrity judges and M.C. Brad Brown of Blue Frog Bakery. All proceeds benefit Shultz's Guest House. You must register IN PERSON. Entry Fee is $10. <ul><li>12:00 PM – Registration at First Baptist Church.</li><li>1:00 PM – Parade starts.</li><li>1:30 PM – Fashion Show and Judging starts at Loring Greenough House.</li></ul>We are grateful for the sponsorship of TCB – The Cooperative Bank; CORE + SEED; and TD Bank! The parade is hosted by JP Centre/South Main Streets and the JP Business &amp; Professional Association. Rain date is Sunday, October 26, 2025.

First Baptist Church

Wine & Wreaths Fall Fundraiser

Create your own wreath and support JP Centre/South Main Streets at the same time! Join us for an evening of DIY wreath making while enjoying wine, cider, donuts, and other fall snacks. Your ticket includes a grapevine wreath, ribbon, a selection of picks for your wreath, and a complimentary alcoholic beverage. Volunteers will be on hand to show you how to make a bow, construct your wreath, and pour your drinks! We will also have a raffle and a silent auction of amazing gifts from our local merchants, along with a chance to earn more decorative picks for your wreath. Complimentary hors d'oeuvres, pastries, and non-alcoholic drinks are included. You must be 21+ to attend. All proceeds benefit JP Centre/South Main Streets. We are a community-led organization whose mission is to enhance and strengthen the JP Centre/South business district as a vibrant center of commercial and community activity for Jamaica Plain and surrounding neighborhoods.

Eliot Hall

South Street Fiesta

Thursdays in July/Jueves de julio July 10, 17, 24, 31/ 10, 17, 24, 31 de julio 6:00 – 9:00 PM 125 South Street, Jamaica Plain Join us for an outdoor concert series on South Street, along with dancing, food, sales, discounts, and special at our local South Street businesses! Free to attend, open to all! Acompáñenos a una serie de conciertos al aire libre en South Street, con baile, comida, ofertas, descuentos y ofertas especiales en nuestros negocios locales de South Street. ¡Entrada gratuita y abierta a todos!

South Street Apts

Blossoms & Sweets

Join us for our Spring fundraiser, where attendees will craft their own flower arrangements with instruction from Deirdre McKenna of Sweet Pea &amp; Sage at 166 South Street. We will have sweet desserts and cocktails, along with coffee and tea to ensure a great night for all. We will also have flower-themed items up for auction, including art, arrangements, and more. There are two seatings for the flower arranging class and cocktails: 6:00 - 7:30 pm and 7:00 - 9:00 pm. Please choose your ticket accordingly. Must be over 21+ to attend. All proceeds benefit JP Centre/South Main Streets programming.

Spring Beer & Trolley Tour

Join us on this hop-on, hop-off trolley tour. Includes tastings at local breweries, eateries, or wine bars; light appetizers at each location; and a history tour on the trolley. Trolley will visit locations in Hyde Park, Roslindale, JP Centre/South, and Egleston Square. Attendees can start their tour at any of the 4 stops - please choose your ticket according to your starting location.  Tickets are limited, so get yours today! explore.jpcentresouth.com/events/ Participating locations Jeanie Johnston Pub Drawdown Brewing Antonio's Bacaro TBD (Roslindale)

Jeanie Johnston Pub

Galentine's Wine & Chocolate Tour

An evening of wine &amp; chocolate, combined with self-love and lots of shopping. Galentine’s Wine &amp; Chocolate Tour is an evening of wine &amp; chocolate, combined with self-love and lots of shopping. Join us on Thursday, February 6, from 5:00 to 8:00pm for a night of shopping, wine, and chocolate! Attendees will receive a map to participating locations where they will receive a variety of treats, along with some great deals in-house. It's called Galentine's but ALL GENDERS are welcome! Kick the night off at our check-in location with a selfie station and music. Tickets are limited so get yours today!

Jamaica Plain

JP Holiday Light Show

Come see the only holiday projection show in Boston! The JP Holiday Light Show will run every evening from 5:00 – 9:00pm, from Saturday, December 7 until Saturday, January 4, 2025. Shows will occur on the hour and half hour. Music is available through your mobile device – be sure to scan the QR code at the beginning of the show. Launch Party on Saturday, December 7, starting at 4:30pm We will have treats and hot cocoa, as well as local holiday music, as we wait for the debut of the JP Holiday Light Show!

Books & Bites Fall Fundraiser

Join us for a literary event and signature cocktails! This year, we decided on a literary theme because we didn’t realize that we had so many renowned authors in Jamaica Plain. We are hosting a panel discussion with these JP-based authors who will talk about their work and relationship with Jamaica Plain. The program will be about an hour and 15 minutes, and then we’ll break for meet &amp; greet and book signings. Guests will be able to enjoy special SIGNATURE COCKTAILS as they meet the authors. Right now, we have three confirmed speakers:<ul><li>Prize-winning author and professor <a href="https://johnfulton.net/">John Fulton</a>, author of The Flounder,</li><li>National Bestseller <a href="https://www.theadamwhite.com/">Adam White</a>, author of The Midcoast,</li><li>Mark Twain American Voice winner <a href="https://www.jennifer-haigh.com/">Jennifer Haigh</a>, author of Mercy Street,</li><li>New York Public Best Book 2022 winner <a href="https://www.neemaavashia.com/">Neema Avashia</a>, author of Another Appalachia.</li></ul>Books will also be on sale from our local bookstore, <a href="https://papercutsjp.com/">Papercuts JP</a>, for authors to sign.

Footlight Club

Oktoberfest Trolley Tour

Pub &amp; Brew Trolley Tour Get our your Lederhosen and Dirndl dresses and join us for a trolley tour of three neighborhoods and their beer. Board the trolley for a three-hour tour and visit:<ul><li>Jamaica Plain - Oktoberfest at Hive Events at Loring Greenough;</li><li>Hyde Park - Roundhead Brewing;</li><li>and West Roxbury - Corrib Pub.</li></ul>Each stop includes free snacks with your purchase of beverage. Trolley will feature history of brewing in Boston and local sites, with Michael Reiskind of the JP Historical Society. Revel in Oktoberfest with songs and toast with Prost! We're serious about the Lederhosen and Dirndl dresses - we want to see 'em! Trolley is a round-trip tour with 3 different starting points. Please select your ticket based on your starting point. You will end your tour where you start. Starting times are listed on your ticket.

Loring Greenough House

South Street Nite Market

Shopping, food, music, &amp; more! Free and open to all. #jpnitemarket

South Street Mall & Tennis Courts

Legal Vitamins for Businesses

An interactive workshop to minimize your business' legal risks. This interactive workshop is designed to help business owners understand the preventative steps they can take to avoid legal problems in the future. Participants will learn how to conduct a mini legal self-audit of their business operations to minimize risk, when to call – and when not to call - a lawyer, and practical tips they can use immediately to reduce their legal spend. This workshop is led by Jan Glassman of Daily General Counsel™. Daily General Counsel™ is a Massachusetts Professional Limited Liability Company and is a City of Boston Certified Women-Owned Business. It was founded by Jan Glassman in 2012 in order to help small businesses, startups and non-profits who, out of choice or necessity, do not ordinarily seek the advice of a lawyer for their legal-related business problems. A working lunch will be provided.

The Footlight Club

SOL-Inspired Mini-Fest

Experience a Day of Inspiration and Wellness at Sol Inspired! Music and Entertainment, Food, Vendors, Live Art, and more! Free and open to the public.

Voices of Liberation

Elevate with AI

Elevate your business with AI tools. For established businesses and professionals - learn about AI tools that help you reach customers/prospects more effectively and scale up your business, whether you are brick-and-mortar, online, service-oriented, or retail. Free and open to all, complimentary coffee and pastries. The workshop will be led by David Wallace.&nbsp;David had a 15-year career as a reporter, editor and columnist in South Florida and Philadelphia before moving to Boston, where things (and journalism) took a turn for the worse. He has worked for newspapers, magazines and their websites, business school professors and book projects, and even taught news reporting tech/media as an adjunct at Emerson College and BU.&nbsp; As a consultant since launching Gamechange LLC in 2009, he has worked with start-ups and solopreneurs, managed a family-owned travel company for several years, upgrading its tech and marketing, and even for household-name corporations like Verizon, SAP and The Wharton School.

Jamaica Plain Branch of the Boston Public Library 

Taste & Tour JP

Join us as we walk the neighborhood, visit six of our favorite restaurants, and learn as we go with tidbits from Jamaica Plain’s history. Attendees will be put into six groups of 10, for a max of 60 attendees. Each group will visit six (6) different eateries in our district and enjoy a “taste” from each place. As we travel from taste to taste, attendees will enjoy a walking history tour of Jamaica Plain. Confirmed locations:<ul><li>Tonino’s – <a href="https://www.nytimes.com/article/best-restaurants-boston.html">recently featured in the New York Times!</a> </li><li>Tres Gatos</li><li>Blue Frog Bakery</li><li>Shea Butter Smoothies</li><li>JPizle Kitchen</li><li>and more!</li></ul>The event will conclude at tour headquarters at JPizle Kitchen/Colombiana with two complimentary drinks for attendees! All funds raised will benefit JP Centre/South Main Streets programs, such as our Canine Costume Parade, Holiday Light Show, Holiday Stroll, and grant and assistance programs for our local businesses.

Jamaica Plain Rentals & Sales

LuMeNet: Black History Month

Small business owners, entrepreneurs, and anyone interested in running their own business can join us for mentoring and networking. This month, we are focusing on Black Women business owners, courtesy of our own board members:<ul><li>Nicole Gunn, Owner Cada Dia Drinkmasters and chair of Uplift JP</li><li>Brie Pullum, Owner VX at 668 Centre Street</li></ul><a href="https://explore.jpcentresouth.com/events/lumenet-black-history-month" target="_blank">RSVP Now</a> Meet others on the same path and ask your questions about your own business journey. Lunch is complimentary. Open to all and free to attend.&nbsp;<a href="https://explore.jpcentresouth.com/events/lumenet-black-history-month" target="_blank">Please RSVP</a>&nbsp;so that we may plan accordingly. Please contact our<a href="https://jpcentresouth.com/contact-us/" target="_blank">&nbsp;Executive Director</a>&nbsp;if you have any dietary restrictions or require any special accommodation.

S22: conversations

Wondering what to do in Boston? Places to eat? Free activities? Good for a group? Date night spot? Girls night out? The best things to do? Ask Joyraft!

Best places to go in Boston? Things to do? Places to eat?

Questions & answers about things to do in Boston

Recs 💬

Community recs 💬

S4: top picks

The most fun, cool and unique things to do in Boston. Can’t miss events, shows and experiences. Concerts, restaurants, bars, free things in Boston and beyond.

The most fun and cool events happening around Boston

Hot and new things to do in Boston

Hot & new

Hot & new 🔥

S11: happening this weekend

What to do in Boston this weekend? From festivals, concerts, performances, free events, screenings and more, Joyraft has the best things to do in Boston.

25+ things to do in Boston/Cambridge/Somerville this weekend

Things to do in Boston this weekend

This wknd

This weekend for you

S21: roundups

Our top picks: outdoor dining, free events, spring festivals, best bars, upcoming concerts, museum parties - the latest in and around Boston.  Slug: joyraft-top-picks-best-things-to-do-boston-ma

Top picks of the best things to do in and around Boston

Joyraft picks: Boston’s best things to do

Roundups ⭐️

Curated by Joyraft ⭐️

S28: calendar experiences

This week in Boston

This week in Boston 📆

This week 📆

S20: c+d experiences

Discover new, unique events and experiences happening in and around Boston. Perfect for date night, good for a group or with a friend. Be the first to know.

The newest events happening in and around Boston

The newest events on Joyraft

Just added

Just added to Joyraft

S16: editor picks

The most unique and can’t miss things coming up in Boston / Cambridge / Somerville and beyond. Festivals, food, drinks, fairs, concerts, art and free activities.

Unique and Can’t Miss Things to Do in Boston

Can’t-miss things to do in Boston 🚨

Can't-miss things to do 🚨

S2 (A): top experiences

The most popular things to do on Joyraft. Concerts, restaurants, bars, events, parties, openings, kid friendly, date ideas, free things in Boston and beyond.

Top 20 things to do in Boston

Top 20: Joyraft’s most popular

Top 20

Top 20 on Joyraft

S3 (A): trending experiences

Discover can’t miss events and things to do in Boston. The most fun, unique and cool events coming to the Boston area this spring and summer.

The hottest events happening in Boston

Trending events on Joyraft

Trending 📈

S17: interest based

Your guide to everything free in and around Boston. From events, to fairs, to festivals, to outdoors. Joyraft has all the free events happening near you.

100+ free things to do in Boston and beyond

Free things to do in Boston

Free things to do

S19: interest based

Kid-friendly events in Boston

S18: interest based

Where to eat and drink in Boston? Joyraft has Boston’s newest bars, restaurants and specials. Drinks and pre fixe dinner menus. Cambridge & Somerville too.

Where

joyraft.host65022

Experiences