What to do in Boston this weekend (Oct 17 - 19)

If you have an event, new attraction, new hotel, or restaurant opening you’d like me to cover, don’t hesitate to contact me.

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Urban Grape closes after 13 years. The wine shop abruptly closed its doors last week after negotiations with its lending bank fell through, according to an Instagram post. The owners promised they would be “returning to the table,” great bottles of wine in hand, in the future. With their weekly free wine tastings and other community events, Urban Grape was a cornerstone of both the South End and the greater Boston wine community.

Related: Why wine still matters. (SWURL)

Chik-fil-A is coming to Boston-Logan. After promising to expand more in the Boston area earlier this year, Chick-fil-A announced it will be coming to Boston Logan International Airport’s E terminal. Customers will be able to enjoy their favorite fried chicken Monday through Saturday, starting in early 2026. (Boston.com)

New Hidden Cocktail Bar opens in Cambridge. Tucked inside Top Mix & Bar, you’ll find CoCoMango Speakeasy: a cocktail bar with 1920s vibes serving up Latin-Caribbean-Asian inspired dishes. As Rachel Blumenthal reviews, the “cocktails are transportive” as is the decor, including the entrance, which involves an “old-timey elevator gate and gold coins.” (Boston Magazine)

The CITGO sign is moving — sort of. If there’s a piece of the Boston skyline that’s more iconic than the Custom House clock tower or Prudential Tower, it’s the Citgo Sign. Glowing white and red over Kenmore Square, there’s no denying that this piece of old advertising memorabilia has become a beloved piece of Boston. That’s why the sign will be raised 30 ft higher and moved 120 feet to the east as part of a project to preserve and restore the corridor. (WCVB)

Two (underrated) museums, one admission. If you’re looking for a sign to visit the Isabella Stewart Gardner Museum, this is it: they’re teaming up with the Boston Athenaeum to celebrate Boston artist Allan Rohan Crite. From October 23 through January 24, 2026, your Isabella Stewart Gardner ticket will also get you past the first floor of the Boston Athenaeum.

No King’s Day returns October 18. Thousands are expected to gather across the country on Saturday to protest the current administration’s “abuses of power, cruelty, and corruption.” Over 400 protests are planned in Massachusetts alone, including on Boston Common, where Mayor Michelle Wu is set to headline. (Boston.com)

Vote for your favorite Icons of Franklin Park Poster. The competition has been whittled down to the top 10, but now you need to choose which you like best. The winner gets $2,000 and a display at City Hall. Vote now!

Sheraton Boston debuts 60s-inspired suite (with Charles River views). As part of their $100 million renovation, and in celebration of their 60th anniversary, Sheraton Boston unveiled a new 60s-inspired suite. Guests can enjoy newly updated modern amenities alongside authentic vintage details and memorabilia from the hotel’s opening year, including a curated vinyl collection (complete with a working vintage record player), AM radio, and vintage television. From now through April 2026, guests can book The 1965 Experience, which includes a whimsical welcome gift and two tickets to View Boston. (savor + roam)

October hotel prices put Boston in second for the world’s most expensive stays. Travelers are flocking to Boston this month, pushing the average hotel price to around $375 per night. (Boston.com)

Condé Nast Traveler readers name three New England ski resorts as the best in the country. For their 38th Annual Readers’ Choice Awards, Condé Nast Traveler released a list of the best 30 ski resorts in the country. Bretton Woods (NH), Killington Resort (VT), and Stowe Mountain (VT) are considered some of the best places for a ski trip by Condé Nast readers. (CN Traveler)

Boston Logan unveils new therapy program ahead of the holiday travel season. There is a new way to let go of travel stress that doesn’t involve building up a bar bill. BOS PAWS is bringing therapy dogs (Remington, a Giant Schnauzer; Buster, a Highland Terrier; and Waffles, a French Bulldog) to Boston Logan’s terminals. This amenity is part of Boston Logan’s goal of becoming a “top-five mega airport in the next three years,” according to Massport CEO Rich Davey. (Boston.com)

Major airports refuse to play Kristi Noem’s video. Airports in cities across the country — including Boston, Atlanta, New York, Phoenix, and more — are refusing to play a video with a message from Homeland Security Secretary Kristi Noem. In the video, Noem blames Democrats for the current federal government shutdown and its impact on TSA operations. According to the 1939 Hatch Act, federal employees are severely restricted or prohibited from engaging in political activities on government premises. (NBC News)

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Everything here is happening this weekend only. Scroll down for recurring events every Friday, Saturday, and Sunday in Boston. For more ideas of what to do, check my Boston Guide.

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Boston Symphony Orchestra presents Tchaikovsky Symphony No. 5 and Adams Violin Concerto with their 2025 - 2026 artist in residence, Augustin Hadelich, from Thursday, October 16, through Saturday, October 18, at Symphony Hall (301 Mass Ave, Boston, MA 02115). Tickets range from $48.99 — $158.99, including fees.

The Head of the Charles Regatta returns to the Charles River for its 60th year from Friday, October 17, through Sunday, October 19. It’s free to spectate, and you can catch views of rowers racing up and down the Charles River from Eliot Bridge and the Weeks Footbridge.

Emmerse yourself in Erroyln Wallen’s Dido’s Ghost (2021) on Saturday, October 18 (7 pm), and Sunday, October 19 (2 pm), at Thomas Tull Concert Hall at MIT (201 Amherst St, Cambridge, MA 02132). This haunting chamber orchestra explores “the lingering echoes of love and betrayal,” setting Purcell’s original Dido and Aeneas as a dream sequence around which Wallen’s work wraps itself. Tickets range from Pay What You Can to $77.25.

Party all weekend at the Left of the Charles Music Festival on Saturday, October 18, and Sunday, October 19, from 12 to 7 pm at The Charles River Speedway (525 Western Ave, Boston, MA 02135). Over 100 indie acts will perform, joined by more than 100 vendors selling art, vinyl, vintage items, and other unique items. Entry is free. Food and beverages will be available for purchase from Notch Brewing, Pizza Project, The Koji Club, Salsa Shack, and more.

The Greenway Fall Movie Night series continues on Friday, October 17, with an outdoor screening of Twilight (2008) beginning at sunset (around 6:30 pm) on the Greenway between India and Milk Street. This is a free event, with free popcorn and candy provided while supplies last.

Do you ever wonder why you can’t stop watching White Lotus? Join Boston Graduate School of Psychoanalysis (1581 Beacon St, Brookline, MA 02446) faculty members on Friday, October 17, from 7 to 9 pm, for Not Quite Paradise: HBO Max’s The White Lotus, the first of their The Power of Drama: Why Do We Watch What We Watch? Community Learning series. A panel of BGSP faculty will look at the complexities of the White Lotus characters, their inner struggles, and the many themes the show explores. This is a free, hybrid event. You may attend virtually or in person.

Head to Seaport for an evening of haunted harmonies and Halloween fun at Play it by Fear on Friday, October 17, from 6 to 8:30 pm at The Rocks (111 Harbor Way, Boston, MA 02210). Glass Arists will be covering Halloween and slasher classics, while Castle Island Brewing and Puffy Clouds Boston serve up treats and brews. Little Words Project will also be on site with their new Nightmare Before Christmas collection. This is a free event with food and drink available for purchase.

Get in the spooky spirit at the Femmetastic Halloween party on Friday, October 17, at Midway Cafe (3496 Washington St, Jamaica Plain, MA 02130), from 10:30 pm to midnight. Dress to impress; there will be a costume contest while The Femmes rock out to spooky songs on stage. Tickets are $17 (with fees). Doors open at 9:30.

Pumpkin isn’t the only spice blend beloved by Bostonians, and to celebrate, the city is hosting a Spicetober Fest on Saturday, October 18, from 4 to 10 pm in Boston City Hall Plaza (1 City Hall Square, Boston, MA 02203). Over 40 vendors will be on hand showcasing Boston’s diverse cultural and culinary community, including everything from harvest-season spices to hot, bold flavors that will make you sweat in the middle of winter. Plus, enjoy Urban Farm demonstrations, chef demos, cocktail-making competitions, mocktail and cocktail demos, and more. Entry is free. Food and beverages will be available for purchase.

Join Petrova Chocolates (61 Salem St, Boston, MA) for a Georgian — the country, not the state — wine tasting at an intimate Meet the Importer with Saperavi Brothers Wine Merchants on Saturday, October 18, from 12 to 3. This is a free event. No ticket required.

Celebrate cider season at Time Out Market Boston Cider Fest on Saturday, October 18, from 1 to 5 pm, at Time Out Market Boston (401 Park Dr, Boston, MA 02215). A DJ will be on hand to keep the vibes right as you sip and sample from some of the market’s favorite cideries. Entry and samples are free. Additional food and beverages are available for purchase from market vendors.

Relive the magic of Scholastic Book Fairs at the Autumnal Grown-Up Book Fair on Saturday, October 18, from 2 to 6 pm at Aeronaut Brewing Company (14 Tyler St, Somerville, MA 02143). Grab a beer and browse a curated collection of books supplied by Porter Square Books, plus all the fun gift items (think: mood rings, socks, etc) that were book fair staples. Entry is free. Food and drink (and books) are available for purchase.

Whether you’re goth year-round or you’re getting in the spirit for Halloween, don’t miss Goth Yoga on Saturday, October 18, at Deep Cuts (21 Main St, Medford, MA 02155) with Crystal Rose. Flow to a curated collection of Joy Division, Tempers, The Cure, Boy Harsher, and more. Tickets are $32.78 (with fees), and include one beer, non-alcoholic drink, or $10 cocktail credit.

Unplug, unwind, and touch clay at the Ceramic Mug Making Workshop with Pottery with a Purpose at Travelmug Cafe (50 Liberty Dr, Boston, MA 02128) on Saturday, October 18, from 12 to 2 pm. Tickets are $117 and include all supplies, a hands-on workshop, glazing and kiln firing (plus shipping), so you can drink out of your mug, and a complimentary drink from Travelmug Cafe. $1 from every ticket is donated to mental health initiatives.

The Huntington Theatre (264 Huntington Ave, Boston, MA 02115) is literally setting the stage to host the Boston Women’s Market on Saturday, October 18, from 11 am to 4 pm. Shop over 20 local, women-owned brands and discover new jewelry, home goods, self-care gifts, and more. This event is free to attend.

Join Boston Girls Who Walk for a Hot Girl Walk around Beacon Hill on Sunday, October 19. The plan is to meet at 10 am in front of the Massachusetts State House (24 Beacon St, Boston, MA 02133) and then walk around the neighborhood to check out the Halloween decorations. This is a free event.

Fruit and vegetables aren’t the only things being harvested right now. Head to Arts at the Armory (19 Highland Ave, Somerville, MA) for Wicked Good Aht Mahket — Harvest Edition on Sunday, October 19, from 12 to 5 pm. Browse and shop art from over 30 local artists. Entry is free. No ticket required.

Read My Lips Boston and Book Ends Winchester are presenting a Spooky Popup Market this Sunday, October 19, from 12 to 4 pm at Remnant Satellite (877 Cambridge St, Cambridge, MA 02141). Grab a delicious brew and shop a curated collection of romance novels centering BIPOC, queer, disabled, plus-sized, and other marginalized voices, plus spine-tingling spooky season reads.

Step behind the curtain at the Wang Theatre’s 100th Birthday Celebration on Sunday, 19, from 10 am to 4 pm. All day long, visitors will have the opportunity to attend workshops, watch live music, take a spin of the prize wheel, bid in the silent auction, and take a once-in-a-lifetime photo on the Wang Theatre stage. Entry is free. Food and drink will be available for purchase from food trucks.

We’re firmly in autumn, and to celebrate, Atlantic Wharf is hosting Fall Fest on Sunday, October 19, from 10 am to 12 pm at Waterfront Plaza (290 Congress St, Boston, MA 02210). There is a full line-up of free events, including apple cider & donuts (while supplies last), live music, instrument petting zoo, magicians, pumpkin decorating, and more.

Boston Symphony Orchestra kicks off the beginning of the 2025 - 2026 season with Brahms’ Piano Concerto No. 1 at Symphony Hall (301 Mass Ave, Boston, MA 02115) on Sunday, October 29, beginning at 3 pm. Tickets range between $41.99 and $134.99 (including fees).

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As a reminder, the Commuter Rail has $10 weekend passes, which give the ticket holder unlimited travel on Saturday and Sunday. The pass is activated during your first trip on Saturday and remains active until Sunday night.

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Taste your way through Back Bay with a Back Bay Evening Chocolate Tour. For $55, take a guided walking + tasting tour of one of Boston’s most beautiful neighborhoods while learning about Back Bay’s historical and architectural significance. Plus, enjoy tastings at four different locations where you’ll sample hot chocolate, cookies, cupcakes, and cake from Back Bay’s most iconic establishments.

Learn the real history of Salem with a Salem Witch Tour from Boston: History, Hysteria, & Handcrafted Brooms. These guided tours begin at Boston’s North Station and take you through the streets and history of Salem before ending in a private broom-making workshop (including a custom spell). Tickets are $149 - $159 and include a round-trip train ticket, broom-making class materials, spell satchel, and guided walking tour of Salem.

You can find a full rundown of recurring walking tours, food tours, bus tours, and trolley tours of Boston in my Beginner’s Guide to Boston.

Start your weekend with a dose of wellness at The Hidden Art Gallery (25 Myrtle Street) in Beacon Hill, which hosts weekly Explore Meditation with Watercolor classes. Held every Friday from 3 pm - 6 pm, learn the basics of meditation while intuitively creating with watercolor. Classes are $55.

Ease into the weekend with a Friday Yoga Flow for all levels at Boston Public Library Honan-Allston Branch (300 N Harvard St, Allston, MA 02134) every Friday through September 19 from 3 to 4 pm. This event is free, but registration is required as each class is customized to participants’ preferences. Yoga mats, blocks, and straps will be provided on a first-come, first-served basis.

Surround yourself with skyline views during a Saturday Community Yoga session at Rooftop@Revere, on top of Revere Hotel Boston Common (200 Stuart St, Boston, MA 02116), every Saturday from 10 - 11 am. Tickets are $10 and include a post-session smoothie.

Every Saturday from June 21 through September 6, start your weekend with the Sweat and Sip Summer Yoga Series on the rooftop of High Street Place (100 High Street, Boston, MA 02110). Classes are $20 and include a $10 voucher to spend at any of the High Street Place Food Hall vendors.

Reconnect with your ability to digest and rest during a Sound Bath Meditation with Ramon of Ib and Flow (247 Walnut St, Brookline, 02445). Sessions ($50) are held every Sunday.

Wind down from the weekend and prepare for the week ahead with a Grounding Meditation session every Sunday from 5 - 6 pm at Blissful Monkey Yoga Studio (663 Centre Street, Boston, 02130) in Jamaica Plain. Led by Licensed Mental Health Counselor Brennan Mallonnee, you will be guided through techniques on how to calm stress responses and practice trauma-informed grounding techniques for anxiety. Tickets are $20. Yoga mats, cushions, and blankets are available, but you can bring your own.

If you’re trying to bring balance into your life this year, start your Sunday brunch with a gentle yoga flow with Brewery Yoga at Lamplighter CX. The class is held every Sunday from 12:30 - 1:30 pm at Lamplighter Brewing Co.’s CX location (110 North First Street, Cambridge, 02141) in their upstairs taproom. Tickets are $25 and include a beer token or a complimentary non-alcoholic drink.

If you’ve always wanted to learn how to navigate Boston by bicycle but have been too intimidated to start, join a Weekend In-And-Back Guided Ride with A Better City TMA. On Saturdays and Sundays from 9 am to 1 pm this spring and summer, join a free, three-hour bicycle ride from one of the many bike paths outside the city (meeting location disclosed upon sign up) and traverse the Urban Loop through downtown before returning to the start location.

If you need a weekend pick-me-up, come to The Moxy Boston Downtown (240 Tremont St, Boston 02116) for Rooftop Yoga on Saturdays and Sundays from 9 - 10 am. Led by Julianne Maquire (Saturday) and Claire Metrick (Sunday) from YogaHub, you’ll flow through a dynamic vinyasa yoga experience, expending energizing movement with breath and community. Tickets are $25.

Whether you already love screenprinting or are completely new to this printing method, DARK MODE hosts DIY Screenprinting workshops at their storefront in Bow Market (1 Bow Market Way, #24) in Somerville on Friday (7 pm) and Saturday (6 pm and 7 pm) nights. Tickets are $45, including t-shirts.

DARK MODE also hosts Candle Making and Intention Setting Workshops every Thursday at 7 pm in their storefront at Bow Market in Somerville. Tickets are $50.

Spend your Friday learning to make classic Italian cuisine with Self Up Cooking Classes (19 Kingston St) in Downtown Crossing from 6 pm - 9 pm. Every week, they host an Italian Dinner with Tiramisu Finale cooking class and dinner experience, where you can learn how to make a three-course meal, including a luscious tiramisu for dessert. Tickets are $100 and include all ingredients.

New to natural wines? Don’t miss the free wine tastings at Petrova Chocolates (61 Salem Street, Boston, MA) in the North End every Friday (3 - 7 pm) and Saturday (12 - 3). Each week, they open bottles of Eastern European natural wines from countries like Georgia, Bulgaria, and Greece. These tastings are free and require no tickets or reservations.

Love Child hosts free wine tastings every Friday from 5 pm to 7 pm and Saturday from 12 pm to 3 pm at their South Boston location (364 West Broadway, Boston, MA). These tastings are free and require no reservations.

Coffee lovers, this one is for you. Every Friday at 10 am, Counter Culture Coffee (374 Somerville Ave) in Somerville opens their Training Center for free coffee tastings. Anyone can learn and connect over perfectly brewed, high-quality, sustainable coffee.

Come to DeLuca’s Market Wine Cellar (11 Charles Street, Boston, MA 02114) in Beacon Hill for a free wine tasting every Friday from 4 - 7 pm. Every week, resident wine expert Donovan handpicks a mix of familiar favorites and bottles from up-and-coming vineyards or hard-to-find vintages to share among participants. No ticket is required.

On Saturdays, Boston Harbor Distillery (12R Ericsson St, Boston, 02122) leads VIP tours ($50) and barrel-side tastings of their spirits ($20).

Come to The Urban Grape (303 Columbus Ave) in the South End on Saturday for The After Brunch, between 2 pm and 5 pm, for their weekly free wine tasting.

Shop local artisans every Thursday and Friday at the Downtown Boston Arts Market. Located in Downtown Crossing (8 Summer St, Boston, MA 02110) between Macy’s and Roche Brothers, this outdoor market will recur weekly from 11 am until 5 pm until October 24.

The Boston Open Market returns to Boylston Street, between Arlington and Charles (across from the Boston Public Library), every Saturday through October from 12 to 5 pm.

Alongside the Boston Waterfront, shop over 50 vendors at the Greenway Artisan Market on the Rose Kennedy Greenway. Beginning May 3, the market will be held every Saturday from 11:00 a.m. to 5:00 p.m. and every Saturday and Sunday beginning June 1.

Jamaica Plain holds its weekly Farmers Market every Saturday from 12 pm to 3 pm year-round in the Bank of America parking lot (677 Centre St, Jamaica Plain, 02130).

The Unique Square Farmers Market returns for their 21st season in Somerville’s Union Square Plaza (66-70 Union Square Plaza, Somerville, MA 02143) every Saturday through October 25 (except Sept 20).

One of Boston’s largest open-air markets, SoWa Open Market (500 Harrison Ave, Boston, MA), is held every Sunday from 11 am - 5 pm until October 26. Stop by to shop with various regional and local vendors, including food and beverage trucks.

Shop the Seaport Summer Market (88 Seaport Blvd, Boston, MA 02210) every Saturday and Sunday from 11 am to 7 pm. Like the winter market, the summer market is filled with unique vendors selling a wide range of items, from original artwork to pet supplies. Food and beverages will also be available for purchase, along with a DJ and a game area for all ages.