See and Do

Weekend Picks – October 2nd

DOTober Dining on District 

Enjoy a fall weekend Dining on District — stroll, shop, sip + dine in the expansion area of South Bay. Snag a picnic table, (painted by the Boys and Girls Club of Dorchester), enjoy music and good eats from one of our many dining options. Take your pod and pups to our dog park, playground and outdoor library. District Avenue will be closed to cars for the weekend. For more information, visit bostonsouthbay.com.  Takes place this Saturday and Sunday, October 3 + 4 beginning at noon. 

Shopping in Seaport

Black Owned Bos. is a platform to highlight and lift local Black owned businesses, places, spaces and the people moving the culture forward.  Shop their outdoor market in the Seaport neighborhood on Saturday. You can reserve your safe and socially distanced shopping spot from 11:00pm-4:00pm here.

Chicken + Waffles

Help out Chez Vous – Boston’s Legendary Roller Rink – by attending their Chicken + Waffles event on Sunday, October 4th from 2-6pm.  They will also be selling fried dough too! You can learn more here! 

Work From Home at Lucy’s

Bring your laptop to Lucy’s on Friday and enjoy brunch while you “work.” Let’s get this weekend going! Brunch starts at 10am.

Get some Coffee

Whether you like it iced or hot or with cream + sugar or black, here are 7 Places to Get Coffee in Dorchester! 

Patio SZN at the Bowery Bar

One of the best patios around, the Bowery Bar is the perfect spot to enjoy cocktails and apps with friends!

Purchase a T-Shirt

Mo Hanley – a local photographer –  has created a new t-shirt featuring local landmarks wearing masks in an effort to raise money for local organizations doing good in our neighborhoods!  You can learn more here! 

Disco Brunch at Blend

Brunch but make it disco.  Blend is hosting a disco brunch Sundays from 11-3.  Enjoy brunch specials, espresso martinis, killer Bloody Marys, drag queen nonsense and disco beats.  Reservations are strongly recommended. Email luisvarzuaga@gmail.com or call 617-265-8846

It’s Oktoberfest at Dorchester Brewing Co.

Dorchester Brewing Co. is hosting an Oktoberfest celebration from Saturday, September 26th through Saturday, October 3rd! However, it may look a little bit different this year. The tap room will continue with socially distanced seating with contactless ordering but will also be offering DBco Fest Bier lager, limited edition glassware, a special Oktoberfest food menu from M&M BBQ, live music and a decorated Beer Hall that makes you feel as though you were in Munich! PS Show up in authentic German gear (Lederhosen or Dirndl) and get a very special prize!

Burgers and Booze

Boston Burger Co. will be popping up at Boston Harbor Distillery on Saturday, October 3rd from 3pm-8pm! Delicious burgers pair perfectly with craft cocktails!

Pick some apples

We know this year has been strange and stressful to say the least. With fall upon us, activities like picking apples, wandering through corn mazes, and purchasing pumpkins can still be a thing as long as social distancing and face masks are part of the plan. Venture out of Southie and pick yourself a bushel and peck of farm fresh apples. Make sure to check check all orchard’s websites for up to date safety info, restrictions etc. Some require reservations so double check before you head out!  Check out our roundup here! 

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About the Author

Maureen Dahill

Maureen Dahill is the editor of Caught in Southie and Caught in Dot and a lifelong resident of South Boston sometimes mistaken for a yuppie. Hockey mom, yoga enthusiast, lover of red wine and binge watching TV series. Mrs. Peter G. Follow her @MaureenCaught.