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Local Events in and Around Milton You Need to Visit This October!
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Historic soirées, harvest workshops, outdoor markets, and Halloween fun across Milton and nearby 🍁✨
By Bridget Conroy
Coldwell Banker Realty | Milton, MA
As a long-time Milton resident and local real estate agent with Coldwell Banker, one of the things I love most about living on Greater Boston's South Shore is how vibrant our local community becomes in the autumn. 🍂 From historic estate soirées and outdoor markets to family-friendly Halloween celebrations, harvest workshops, and cozy neighborhood gatherings, October is packed with incredible events across Milton, Quincy, Cambridge, Hyde Park, and Holbrook. 🏡
Whether you're looking to explore new neighborhoods, support local women-owned businesses, or spend a scenic weekend out with family and friends, here is your ultimate guide to the top local events happening around the area this month! 🧡
1. 2026 Fort Point Open Studios 🎨
- 🗓️ When: Friday, October 16th (4:00 PM – 7:00 PM) | Saturday, October 17th & Sunday, October 18th (12:00 PM – 6:00 PM)
- 📍 Where: 70 Sleeper Street, Boston, MA
- 🎟️ Admission: Free Admission
Fort Point artists open their historic waterfront studios each fall for a full weekend of touring, meeting local creators, and purchasing original artwork. Visitors can also enjoy free art-making activities, live music, and special community events throughout the historic Fort Point Channel neighborhood. 🖌️
2. Wicked Trivia Weekly at Abby Park 🧠🍻
- 🗓️ When: Every Thursday at 8:00 PM
- 📍 Where: Abby Park, 550 Adams St, Milton, MA
- 🎟️ Admission: Free Admission
- 🔗 Details: Reserve a Table at Abby Park
Looking for a fun weeknight gathering spot right here in Milton? Head over to Abby Park every Thursday evening for Wicked Trivia hosted by Pat Lally! Gather a team, enjoy great food and drinks, and test your knowledge in one of Milton's favorite neighborhood dining spots. 🍔
3. White Pine Vintage Market at Governor Hutchinson's Field 🛍️🌲
- 🗓️ When: Saturday, October 17th | 10:00 AM – 4:00 PM
- 📍 Where: Governor Hutchinson's Field, Adams St, Milton, MA
- 🎟️ Admission: $10 General Admission | Kids Under 12 Free
- 🔗 Tickets: Purchase White Pine Vintage Market Tickets Here
I am so proud to be an official event sponsor for this wonderful Forbes House Museum fundraiser! 💛 Set against the scenic views at Governor Hutchinson's Field, the White Pine Vintage Market features curated craft and antique vendors, a beer garden, food, and live music. Ticket proceeds directly benefit the Forbes House Museum and The Trustees of Reservations.
4. Quincy's Open Heritage Day 🏛️⚓
- 🗓️ When: Saturday, October 17th | 10:00 AM – 4:00 PM
- 📍 Where: Multiple Historic Locations throughout Quincy, MA
- 🎟️ Admission: Free Admission
Celebrate Quincy's rich historic and cultural heritage with over 20 free historic tours, activities, and special programs across 10 historic sites and the USS Salem heavy cruiser! Organized by local volunteers and city groups, this celebration is a fantastic way to explore neighborhood history right next door to Milton.
5. A Spiritualist Soirée at the Mansion 👻🕯️
- 🗓️ When: Saturday, October 17th | 7:00 PM – 10:00 PM
- 📍 Where: Eustis Estate, 1424 Canton Ave, Milton, MA
- 🎟️ Admission: $80 Members | $95 Non-members
- 🔗 Tickets: Reserve Your Soirée Tickets Here
Step back in time at the historic Eustis Estate for a Victorian Spiritualism-themed evening party after dark! Enjoy tarot, ghost photos, parlor games, a séance sketch, food, and drinks. 🔮 Guests are encouraged to wear 1860s–1920s historic attire or gothic dress for an unforgettable autumn evening in Milton.
6. BlueHillsFest 2026: Open House in the Park 🥾🦉
- 🗓️ When: Saturday, October 17th | 9:00 AM – 4:00 PM (Rescheduled Date)
- 📍 Where: Blue Hills Reservation, Milton, MA
- 🎟️ Admission: Free Admission
- 🔗 RSVP & Schedule: Sign Up & View Schedule at Better Blue Hills
Hosted by the Coalition for a Better Blue Hills, this day-long park celebration features guided hikes, weather observatory tours, live animal shows, lawn games, garden tours, outdoor family activities, and free admission to the Trailside Museum. It's an unbeatable family day in Milton's favorite outdoor playground! 🌳
7. Cambridge Explores the Universe 2026 🔭🌌
- 🗓️ When: Saturday, October 17th | 12:00 PM – 4:00 PM
- 📍 Where: Center for Astrophysics, 60 Garden Street, Cambridge, MA
- 🎟️ Admission: Free Admission
- 🔗 RSVP: Register on Eventbrite Here
Become an astronomer for a day! This family-friendly event on Observatory Hill in Cambridge lets visitors experience space science firsthand by meeting astrophysics experts and exploring universe discoveries. 🚀
8. Outdoor Yoga on the Patio with Muscle & Flow 🧘♀️☕
- 🗓️ When: Saturday, October 17th | 9:00 AM – 10:00 AM
- 📍 Where: Two Pence Market, Milton, MA
- 🎟️ Admission: $25
- 🔗 Tickets: Book Your Yoga Spot via Two Pence Market
Start your Saturday morning with a relaxing outdoor yoga session on Two Pence Market's covered patio, led by Eileen Gillis of Muscle & Flow. After class, grab a warm seasonal beverage inside the market! 🍂
9. Tapi Papi Hot Sauce Tasting & Showcase 🌶️🔥
- 🗓️ When: Sunday, October 18th | 4:00 PM – 6:00 PM
- 📍 Where: Two Pence Market, Milton, MA
- 🎟️ Admission: Free Admission
- 🔗 Details: View Event Details on Two Pence Market
Stop by Two Pence Market in Milton Village to meet private chef Fernanda Tapia, founder of Tapi Papi, and sample her amazing, locally made, women-owned hot sauces! Perfect for local foodies looking to bring some bold flavor and spice to their autumn dishes.
10. Lanterns & Legacy Mahjong at the Museum 🏮🀄
- 🗓️ When: Tuesday, October 20th | 6:30 PM – 8:30 PM
- 📍 Where: Forbes House Museum, 215 Adams St, Milton, MA
- 🎟️ Admission: $50/person (inclusive of refreshments; please bring your own 2026 Mahjong card)
- 🔗 Tickets: Register for Mahjong at the Museum
Gather with friends and make new connections during an elegant evening of Mahjong surrounded by the historic charm of the Forbes House Museum. Costumes and masks are encouraged for this festive autumn night out! 🎭
11. Harvest Wreath Workshop 🌾💐
- 🗓️ When: Saturday, October 24th | 10:00 AM – 12:00 PM
- 📍 Where: Mary May Binney Wakefield Arboretum, 1465 Brush Hill Rd, Milton, MA
- 🎟️ Admission: $5 Adult Ticket | Kids Free
- 🔗 Tickets: Sign Up for the Harvest Wreath Workshop
Join neighbors at the historic Wakefield Arboretum barn to design and assemble a stunning autumn harvest wreath using a variety of seasonal foliage, seed pods, and branches. All supplies are included in the workshop price!
12. Fall Foliage Fest at Wakefield Arboretum 🍁🦆
- 🗓️ When: Saturday, October 24th | 10:00 AM – 2:00 PM
- 📍 Where: Mary May Binney Wakefield Arboretum, 1465 Brush Hill Rd, Milton, MA
- 🎟️ Admission: $5 Adult Ticket | Kids Free
- 🔗 Tickets: Register for Fall Foliage Fest
Relish the gorgeous fall foliage across the arboretum grounds! Enjoy pumpkin carving, guided garden tours, and live animal encounters presented in partnership with Mass Audubon. 🎃
13. Milton Halloween Stroll 🎃🍬
- 🗓️ When: Saturday, October 24th | 3:00 PM – 5:00 PM
- 📍 Where: East Milton Square Deck, Milton, MA
- 🎟️ Admission: Free Admission
Brought to you by the Milton Chamber of Commerce, join your favorite local businesses for an afternoon of trick-or-treating and Halloween cheer! Costumes are encouraged for an afternoon featuring a bounce house, live music, face painting, and family fun. 🎶
14. Charcuterie Board Workshop 🧀🍇
- 🗓️ When: Saturday, October 24th | 2:00 PM – 4:00 PM
- 📍 Where: Two Pence Market, Milton, MA
- 🎟️ Admission: $80 Admission
- 🔗 Tickets: Book Your Charcuterie Workshop Ticket
Join resident cheese and charcuterie expert Tori on the covered Two Pence Patio for a hands-on workshop! Learn the art of selecting, pairing, and styling custom charcuterie boards, and take home your own handcrafted board just in time for holiday entertaining. 🥂
15. Trick or Treat Milton 2026 🧙♀️🍫
- 🗓️ When: Sunday, October 25th | 3:00 PM – 5:00 PM
- 📍 Where: First Parish Milton, 535 Canton Ave, Milton, MA
- 🎟️ Admission: Free Admission
Hosted by First Parish and United Congregational Church, this magical free community Trick or Treat event features a bouncy house, festive costumes, and plenty of candy for a spooky seasonal afternoon. 🍬
16. First Friday at the Milton Art Center 🎶🖼️
- 🗓️ When: Friday, November 6th
- 📍 Where: Milton Art Center, 334 Edge Hill Rd, Milton, MA
- 🎟️ Admission: Free Admission
Looking ahead to November, kick off the new month at the Milton Art Center's signature First Friday event! Enjoy a welcoming, family-friendly evening celebrating local art, music, and culture right in the heart of our community. 🎨
Thinking About Making a Move in Milton or the South Shore? 🏡🔑
Living in Milton means having world-class outdoor parks, rich history, and tight-knit community events right at your doorstep—all just minutes from downtown Boston. 🌳
Whether you're looking to buy your dream home, sell a property, or simply learn more about life in our community, I'm always here to help as your trusted local real estate expert. Reach out today or follow along on Instagram @bridgetconroy for more Milton real estate insights and local guides! 📲🧡
