Blog :: 09-2018

Where to Celebrate Oktoberfest in the Boston Area

Oktoberfest, an autumn tradition established long before pumpkin spice

When mid-September arrives, it's usually time to start wearing flannel shirts and leather boots. 

Once the summer's officially over, we start to look forward to their favorite things to do in the fall. Some people just can't wait for the start of football season. Others count down the days until they can order their seasonal pumpkin spice latte. There are plenty of others who enjoy apple picking at a local orchard or decorating their home for Halloween and trick-or-treating with their kids...

And then there's the Oktoberfest crowd. 

Whether you're new to the Boston area or if you're a long-time resident looking for something to do, we're sharing several upcoming Oktoberfest celebrations to check out in Boston and in the greater Boston area:

Harpoon Oktoberfest: September 28-29

Friday, September 28th
General Admission: 5:30pm - 11:00pm
Doors close: 9:30pm

Saturday, September 29th
General Admission: 1:00pm - 7:00pm
Early Access Doors: 12:00pm - 1:00pm
Doors close: 5:30pm

306 Northern Avenue, Boston, MA 02210

Come hoist a pint with us at our Boston Brewery at our biggest festival of the year! You'll join thousands of beer-loving fans during our 2-day festival that takes place outside underneath tents alongside the brewery!


Oktoberfest Yoga Brewha at Aeronaut Brewery: October 6

10:45 am - 12:30 pm

14 Tyler Street, Somerville, MA, 02143

Kick off the Fall season and Oktoberfest at the eccentric space in Aeronaut Brewery with an all levels flow! Brew up your own energy and vitality on the mat and then stay after to enjoy some brews that the team at Aeronaut has dreamed up!


Cambridge Oktoberfest 5K in Harvard Square: October 7

100 Cambridgeside Place, Cambridge, MA, 02141

Join us on Sunday, October 7th @ 9:30 am for a festive German-themed 5k that circles Kendall Square and is immediately followed by an outdoor Oktoberfest on the CambridgeSide roof deck with Notch, Slumbrew & Bantam Cider!


Shovel Town Brewery Oktoberfest: October 13

12:00 pm - 10:00 pm

50 Oliver Street, Easton, MA, 02356

Come join the fun at Shovel Town Brewery's 2nd Annual Oktoberfest to Benefit the Easton Food Pantry! This year’s Shovel Town Brewery’s Oktoberfest is shaping up to be a great event! We are planning to expand the event with a tent in our parking Lot for Games and Food! This year’s event will once again feature live music from several local artists, authentic German Food, Wood Fired Pizza, games and Shovel Town Oktoberfest and Pumpkin Beer and much more!


13th Annual New Bedford Oktoberfest hosted by SCBA: October 13

3:00 pm - 11:30 pm

Pier 3, 106 MacArthur Drive, New Bedford, MA, 02740

The SCBA Presents:  The 13th Annual NB OKTOBERFEST! Proceeds support at-risk youth & educational based charities along the Southcoast. Beer Sampler tickets will be available. Steins available in limited quantity to the first 200 purchasers only.

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5 Family-Friendly Fall Festivals in Boston, MA

Mark the family calendar for these fun fall festivities in Boston and beyond

It can be tough to get back in the rhythm of things after summertime, but the variety of fall family activities can bring everyone back together after long work weeks and busy school days. Cities and towns all over Massachusetts know the importance of a family-friendly social calendar within their communities—it's one of the reasons why the state was named the Best State to Raise a Family earlier this year. 

Here are some favorite local Boston-area fall festivals to bring along everyone in your family: 

Berklee Beantown Jazz Festival

Date: late September

Hosted by the Boston's renowned Berklee College of Music, it's described as "Boston’s biggest block party" that attracts music lovers with a variety of live music performances drawing from jazz, Latin, blues, funk, and groove. For the kids, there's also KidsJam, an instrument petting zoo, and an array of food vendors. 


Allston Village Street Fair 

Date: late September

Labeled as the "Boston's Hippest Multicultural Event," the Allston Village Street Fair invites the entire family to enjoy live music and entertainment, interactive activities and an international food court. Worried about parking? Allston is easily accessible on several T lines and there will be a free shuttle available to the Guest Street Parking Garage in Brighton. 


Nantucket Cranberry Festival

Date: early October 

Escape Boston for the day and head to the coast for family fun in Nantucket. Sponsored by the Nantucket Conservation Foundation, "visitors can expect to learn about the history of cranberry farming on Nantucket through educational displays and harvesting demonstrations, participate in family activities, sample delectable cranberry treats, and other New England classics, or simply enjoy the music and the spectacular autumn scenery." The best part? You can bring some organic Nantucket cranberries to enjoy back home in Boston!


Annual Pumpkin Float at Frog Pond

Date: mid-late October

Bring-your-own carved 8-inch pumpkin to be displayed at Frog Pond in Boston Common! Volunteers will illuminate and place your pumpkins into the pond for a spooky spectacular. This is the perfect event to invite family, friends, and your children's friends for a family fun night out in the heart of Boston. 


The Big E

Dates: mid-September - late September

Based in West Springfield, the Eastern States Exposition (the Big E) is a major festival in the Northeast that offers a variety of music, food, and entertainment for everyone. The Big E spans over two weeks with live performances, food and beverage contests, car shows, circus spectaculars and much more. 

Million-Dollar Listings Available in Jamaica Plain

Jamaica Plain is a classic streetcar suburb that has become one of Boston’s most dynamic neighborhoods.

Surrounded by the Emerald Necklace, Franklin Park, and Jamaica Pond, Jamaica Plain offers plenty of outdoor recreation opportunities and places to hang out on lazy Sunday afternoons. Jamaica Plain is home to a diverse population and is a great place to visit, shop, dine, and live all year round!

Here's our pick of million-dollar real estate listings currently available in Jamaica Plain, Boston, MA:

54 Burroughs Street

Boston, MA 02130

MLS Number 72232060

Basic Information:

  • 4 bedrooms, 4 bathrooms
  • Price: $2,295,000

Luxury and privacy in this exquisite carriage house steps from Jamaica Pond! Fully renovated to the highest standards in 2014, this home has it all! Enter to a dramatic great room with high ceilings, gleaming hardwood floors and fine custom finishes that is wide open to a sensational center-island kitchen featuring stone countertops and top-of-the-line appliances. Large, two-sided gas fireplace separates this from the gracious formal dining room and is a wonderful focal point for both. For someone who loves cooking and entertaining, this space has no equal! Also, office/library, wet bar and mud room on this level. Head upstairs to a wonderful family room with a stunning arched window filling the space with light. Then discover a no-compromises master suite with sitting room, dressing room, sumptuous bath and terrace. Two add'l bedrooms, full bath and laundry complete this floor. The lower level offers a huge home gym and loads of storage. Lovely yard, 2 pkg spaces & guest pkg included


241 Perkins, Unit D-302,

Jamaica Plain, Boston, MA 02130

MLS Number 72339953

Basic Information

  • 4 bedrooms, 2 bathrooms
  • Price: $1,999,000

Welcome to Cabot Estate. Please view our video to learn about this exquisite home and location. This complex is nestled on 23 acres on the Boston-Brookline border. This 24-hour gated community is convenient to the Boston medical centers, museums, restaurants, and other cultural opportunities. This unique renovated unit of 3366 sq. ft. on two levels is the largest in the complex. Enjoy the open floor plan that leads to your own private patio enhanced by lush landscaping and Jamaica Pond. The kitchen features lovely cabinetry, imported granite, and an exotic wood island. Adjacent is a cozy den with its own private balcony and an elegant master bedroom suite. The lower level has 3 bedrooms, 2 full baths, a laundry room and storage. There are 2 tandem indoor garage spaces. Other amenities include a pool, tennis courts, library, exercise, billiard, and function rooms. Walking paths throughout the complex and along Jamaica Pond will keep you in shape and your pet healthy.


46 Pond Street, Unit 2

Jamaica Plain, Boston, MA 02130

MLS Number 72323562

Basic Information

  • 3 bedrooms, 1.5 bathrooms
  • Price: $1,679,000

Wonderfully located on Pond Street near The Boat House, between Centre Street and The Jamaicaway, this beautiful three-bedroom, two and one-half bathroom Victorian-era condominium has undergone a gut renovation while retaining its period charm and character. With over 2,525 square feet of living space on two levels, this unit also provides gorgeous Pond views from interior rooms as well as a large front deck. There is excellent light throughout the residence. Other features include a well-appointed kitchen with Jenn-Air appliances, Goodman HVAC systems, central air-conditioning, basement storage, a garage parking space plus an outside parking space. This property is convenient to local shops, restaurants, parks, and the “T”. It is also within two blocks from a bus line servicing the Longwood Medical Area and Back Bay.


19 Cheshire Street, Unit Right

Jamaica Plain, Boston, MA 02130

MLS Number 72372930

Basic Information

  • 3 bedrooms, 2.5 bathrooms
  • Price: $1,495,000

Last one remaining! Meticulous attention to detail and the highest level of craftsmanship define The Farmhouse Residences at 19 Cheshire Street. Located on a sleepy side street in Jamaica Plain, this new construction dwelling has been crafted to seamlessly meld modern amenities with classic farmhouse details + style. There are 3+ bedrooms and 2.5 bathrooms, dramatic spaces + a timeless design. Highlights include an open floorplan living area, tall ceilings, a magazine quality custom kitchen w/ inset cabinetry, quartz counters and Thermador professional appliances and beautiful bathrooms clad in tile b Jeff Lewis. Classic farmhouse details include beadboard + shiplap walls and ceilings, wide plank hickory flooring, period moldings and hardware by Emtek and Restoration Hardware. The basement is finished as a recreation space/4th bedroom. A full staircase leads to an unfinished attic. An 8' French door leads to a deck and fenced yard area. 1 garage + one surface parking. A must see!


205 Chestnut Avenue, Unit R

Jamaica Plain, Boston, MA 02130

MLS Number 72388779

Basic Information

  • 4 bedrooms, 2.5 bathrooms
  • Price: $1,475,000

Suburban oasis in the heart of JP. Set back off of Chestnut Ave, this impeccably renovated single family is extremely private yet right in the mix of all the best of JP. This home has been lovingly restored and has all the modern conveniences of new construction along with its original charm and soul. Open plan chef's kitchen with granite counters and over-sized island, perfect entertaining space. High ceilings and gorgeous pine floors throughout. Living room with gas fireplace and bay window. Additional, side mudroom entry, separate formal dining, office and half bath complete the first floor. Original newel post and railing leads you to a second level with two additional bedrooms and full bath with tub in addition to a full master suite. Third level currently used for guests and children's playroom offers ample space for two additional rooms and or keep as open loft. All this and gorgeous landscaped yard, patio and deck. Located btw Stony Brook and Green St MBTA.

Interested in any of these listings?

Contact us directly at or give us a call at 617-396-3100. Feel free to visit our website and search through hundreds of listings to find the right real estate for you in surrounding Boston neighborhoods and throughout the greater Boston area. Save your favorites when you register with us and you can get email updates when similar properties that match your criteria are posted. Contact us for more information!


Additional Resources about Living in Jamaica Plain

Best Websites to Follow for Local Boston News

Stay in-the-know with these five Boston local websites

If you're new to the Boston area, we'd like to wish you a warm welcome to the heart of New England! 

We understand that it can be tough to get acquainted with new surroundings—especially if you're not from Massachusetts, let alone New England—so we've picked our top picks for local websites to help you learn more about your neighborhood. Whether you're looking for date night ideas or weekend activities for the entire family, these resources will serve you well:



WickedLocal knows how to bring Boston-area residents the latest news on what's happening in communities across the state. Visit WickedLocal to find the site for your city or town in Massachusetts. 

Boston Magazine

Boston Magazine has been delivering chic lifestyle news to the Boston area since the 1960s. Readers will find current design trends, home entertaining tips, restaurant openings, new real estate developments, and local celebrity interviews. The annual Best of Boston awards show off the best Beantown has to offer in Food & Restaurants, Shopping, Services, Neighborhood Bests and more.  


Want to know what's happening in Boston sports? Add MassLive to your shortlist for Boston media to follow. Bonus: MassLive also has two apps for News and the New England Patriots football team, available for both Apple and Android devices. 

(P.S. If you're not sure where to watch games live downtown, we've put together a list of classic sports bars in Boston.)



BostonCentral offers a comprehensive list of family-friendly happenings within the Boston area and beyond. You'll find helpful information such as "Boston Kids Activites," "Boston-Area Classes-Camps," "Boston Kids Shopping," and "Boston Parenting."  



The Patch's corporate structure has lost some of the local, personalized stories that used to be shared more often, but it is a great resource for important weather updates, road closures, transit cancellations etc. If you're hosting a local community event, Patch users are able to submit press releases and, if approved, will be shared on the website. Search within Patch in Massachusetts to find your city or town. 


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