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Jamaica Plain is bursting with fun activities for any season, but the temperate weather of fall is a great time to get outdoors. Whether this is your first autumn in the area, or your fiftieth, these are the activities and sights you can’t miss.

Boating on Jamaica Pond

Nothing beats the natural beauty of Jamaica Pond in full bloom. And where better to see it than from the water? Courageous Sailing operates rowboat and sailboat rentals on the pond. Don’t worry sailing lessons are also available. If you’re concerned about risking it on the not-so-high-seas, take a stroll or a run around the nature-studded pond.

Identifying Flora at the Arnold Arboretum

One walk through the Arnold Arboretum at the seasonal change and you basically have a degree in horticulture. Not only are the many flowers and trees in the park aesthetically gorgeous, they’re usually identified by nearby plaques for a mini lesson in plant life. Check the schedule before you head over; you may be able to join in on a yoga class or guided tour.

Self-Guided Mural Tour

While the weather is still nice, take a walk through the streets of Jamaica Plain and seek out the many vibrant murals painted around town. Whether you’re in it to snap a few Instagram photos, to appreciate beautiful local art, or as a fun scavenger hunt for the kids, these larger-than-life artworks are sure to do the trick.

Local Shopping on Centre Street

Centre Street is bursting with unique local shops selling everything from high-quality, gourmet chocolate to trendy clothing and accessories. It’s also home to one of the original Boomerangs locations. Boomerangs is a second hand shop that donates its proceeds to the Aids Action Committee. No matter what you buy, you’re supporting the local community!

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The stormy July weather (and most COVID-19 restrictions—let’s hope it stays this way) has finally lifted and Greater Boston residents are ready to flood the streets to enjoy our neighborhoods! Roslindale bursts with excitement in the temperate months and there are more activities to attend than days to spend on them. Whether you’re a new homeowner or a lifelong Rozzie resident, these are the activities you simply can’t miss.

Shop for Fresh Produce at the Farmer’s Market

The Roslindale Farmer’s Market has been named one of the best in Boston and it can’t be beat for locally-sourced ingredients. Every Saturday Roslindale Square becomes packed with vendors from local farms and businesses ready to impart their delicious goods on the neighborhood. Pick up some fresh bread, local produce, and those homemade cookies you have your eye on. Go ahead, indulge—you deserve it.

Jam to the Sounds of Jazz in the Square

Every first Friday of the month local musicians gather in Roslindale Square to serenade their neighbors with sweet jazz melodies. For an admission cost of $10 (free for kids under six) the whole family can dance to the beats of Ella Fitzgerald and Miles Davis. Drinks and snacks are also available.

Enjoy the Sunshine at Turtle Swamp’s Beer Garden

Sip a local brew while enjoying the spring sunshine at Turtle Swamp’s outdoor beer garden. Bring your own food from your favorite Roslindale restaurant and chat with friends or embark on a friendly (sort of) game of bingo. Sometimes the beer garden features live music as well to add to the relaxing environment.

Get in Shape the Social Way

If you’re a fitness junkie or looking to become one, try joining a running group to get fit and meet new neighborhood friends. Parkway Running Club serves Roslindale and West Roxbury and offers multiple group runs per week. The club is open to all ages and skill levels and also hosts track workouts in the nicer weather. Who knows, maybe a supportive team is all you need to become a runner for life.

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One of the most important decisions homebuyers have to make when they’re ready to take the plunge into home ownership is: What area do we want to live in? As the ubiquitous real estate adage goes: Location, location, location!

There are the obvious parameters like price and condition of the home that guide your ultimate decision, but make sure to consider these important factors as well.


If you own a car, you’ll want to consider whether parking is accessible in the neighborhood you’re looking at. Do most homes have onsite parking or street parking? Is that street parking permit parking, or are there parking restrictions for street sweeping (no parking on Tuesdays from 12pm-4pm).

Are the streets usually packed with cars or are parking spots often available throughout the day? What about snow? How will a blizzard or even a few inches of powder affect your parking karma?

You’ll also want to investigate how long it will take you to get to the places you frequent, like your work, the grocery store and common highway routes. If it takes 20 minutes just to get out of the neighborhood, it may not be a good fit. Conversely if you don’t have a car it’s important to note how many public transport options are available, how reliable they are, and where they take you.

School System

This is a notoriously challenging consideration in the Greater Boston area. Towns like Brookline and Wellesley are known for having grade A school systems but they’re prohibitive in terms of price and they’re outside of Boston proper.

Boston Public Schools get a bad rap, but they’re the only option for urban dwellers that can’t spring for private school or don’t want to contend with the “lottery” system of charter schools. The important thing to remember is that not all schools in the same system are created equal. Research the specific school branches in your desired neighborhood to see what their teacher reviews are and what kind of extra support programs they offer their students. The neighborhood may also offer after school programs to supplement school work.

Ratio of Owner-Occupied Homes to Rentals

Especially in Boston, the city of universities, rental-heavy neighborhoods can attract a lot of students and other transient populations. This can mean problems like noise, although not necessarily. But even more importantly, it means you won’t have permanent neighbors.

A larger percentage of owner occupied homes can indicate a more stable neighborhood and perhaps a stronger local community. Homeowners also generally take more pride in their homes and neighborhoods leading to better all around care.

Still having trouble finding the right neighborhood for your next home? Reach out to us at or 617-942-1741 and we’ll help you find the perfect balance.

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