Everything You Can Do in Boston This Weekend

You had us at Dogtoberfest.

Did, like, every single person in Massachusetts go apple-picking this past weekend? Sure as hell felt like it. The weather’s cooler but still beautiful this weekend, so by all means keep hitting up those orchards -- just be prepared for massive crowds. And if your fridge is already groaning under the weight of all those apple crisps, there are lots of other options this weekend. You can revisit a newly reopened beer garden, join the remote rendition of the Roxbury Film Fest, take part in a cycling fundraiser, or celebrate all things puppy-related at Harpoon. In the meantime, as always, continue to support the Black community as well as the local dining, grocer, dispensary, fitness, and drinking scenes. Here is everything you must do in Boston this weekend.

Do right by Oktoberfest at Dorchester Brewing Company

Friday, October 2 - Saturday, October 3
Dorchester Brewing Company
There may not be a live band this year, but there will be a live accordion player. There’s also the ever-quaffable DBco Fest Bier (best enjoyed in a limited-edition stein), brats with sauerkraut, and oversized pretzels with your choice of dipping sauce. Oh, and you definitely want to dress up in your best lederhosen, because prizes await. 
Cost: Free to enter and reservations are recommended

Make like old times and attend the Roxbury International Film Festival

Friday, October 2 - Sunday, October 4
The 10-day festival hasn’t skipped a beat. As the largest fest in New England to celebrate filmmakers and other creatives of color, the event includes shorts, documentaries, and features as well as workshops and live Q&As (which have seamlessly been moved online). And while folks can’t be meeting up in person before and after, the festival organizers have created a list of local POC-owned restaurants that you can order from (and further suggest ordering some drinks from The Urban Grape). 
Cost: $11-13 per movie; $125 for full festival pass

Rejoice at the rebirth of the Trillium Garden on The Greenway

Friday, October 2 - Sunday, October 4
Trillium Garden on The Greenway
Further proof that summer’s not over yet: Trillium’s beloved beer garden has just reopened. Take in the changing leaves while trying small-batch beers brewed onsite -- a new feature this year -- as well as the expected array of Trillium ales. You can contactless-order both beer and food truck vittles, and of course, social distancing will be strictly enforced.  
Cost: Free to enter; make reservations up to seven days in advance at Resy (same-day reservations are also available)

Extend summer at the Summer Shack Harvard Square pop-up

Friday, October 2 - Sunday, October 4
One Bennett Square
Such divine weekend weather demands oysters and then some. The new pop-up from our Summer Shack friends includes plenty of bivalves as well as sashimi, clam chowder, whole belly fried clams, and lobster rolls. And if you can’t make it this weekend, you have a little time: It’s open daily through the end of October. 
Cost: A la carte; seating on first-come, first-served basis

Leaf peep right in your own backyard

Friday, October 2 - Sunday, October 4
Emerald Necklace
Why rent a car and trek up north when you can get your foliage fix in town? The Emerald Necklace boasts more than 8,000 trees, and the conservancy’s mobile guide will take you on a leisurely tour of the various flora amidst the park’s 1,100 acres.
Cost: Free

Go whole hog and order a pig roast to go

Friday, October 2 - Sunday, October 4
Got 10 people in your pod? Good--now it’s time to feed them. Citizen is doing the only to-go pig roast in town, a massive smorgasbord that starts with local oysters and clams before moving on to a whole suckling pig and five seasonal sides. And with wine, beer, and cocktails to go, you can make a party of it without lifting a finger. 
Cost: $580 for 10 people; each additional person costs $58 (if safe!). Must be ordered 48 hours in advance

Enjoy the simple pleasures at the Cisco Brewers Seaport Beer Garden

Friday, October 2 - Sunday, October 4
Just in time for the holiday weekend, our favorite seasonal beer garden has reopened. Pretend you’ve been transported to Nantucket while enjoying your favorite Cisco brew and chowing down on freshly made slices and salads from Oath Pizza. All the usual COVID-19 rules apply; contactless ordering online and via QR code makes things extra easy. 
Cost: Free to enter

Get your early fall fix at The Raw Bar at Island Creek Oyster Farm

Friday, October 2 - Sunday, October 4
We woke up one late spring morning despondent that we wouldn’t get to visit the seasonal ICO raw bar. But then (almost) everyone was terrific about wearing their masks and social distancing, and we were gifted with another coveted seasonal spot. Head down south to savor oysters, beer, wine, and Duxbury Bay views. The menu may currently include only freshly shucked bivalves and beverages, but that’s more than enough for us these days.
Cost: Free to enter

Sweat the good sweat during the OCRA Block Party ride 

Sunday, October 4
Portside at East Pier
In-person charity fitness classes are still few and far between, but thankfully there’s one on the docket this weekend thanks to AXL Boston. The outdoor ride will raise money for the Ovarian Cancer Research Alliance and is part of a larger national “spin soiree” (we’re the only non-virtual class).
Cost: $40; you’ll need to create an account on the AXL Boston site

Revel in the simple pleasures at Dogtoberfest

Sunday, October 4
Oompah -- or is it woofpah? Either way, it’s time for the best part of Octoberfest. Yes, Dogtoberfest has gone virtual, but that doesn’t mean that the costumes will be any less ridiculous. Commit to running or walking one mile with your pup, using the TK hashtag to win prizes throughout the day, and be sure to also enter the Festminster Show on Facebook to win in categories such as Best Kisser and Best Trick. 
Cost: $40 to register (registration includes a Wag Bag which can be picked up at either Harpoon Brewery location--and yes, includes a four-pack of beer)

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Meaghan Agnew is actually happy to put the sweaters away for one more weekend. See how happy by following her on Instagram.