Sold Out—and we’re adding another night! ✨
Thanks to overwhelming demand, we’re opening a waitlist for February 13, the night before our sold-out event provided there is sufficient interest in this alternative date.
Spots for February 13 will be offered to the waiting list first—don’t miss your chance!
👉 Add your name to the waitlist by emailing discovermiddleborough@gmail.com
Scare Your Sweetheart: A Valentine’s Night of Romance and History at The Oliver Estate
Middleborough, MA — February 14, 2026
This Valentine’s Day, couples are invited to experience a date night unlike any other at the historic Oliver Estate in Middleborough. “Scare Your Sweetheart” is a special evening combining indulgent desserts, drinks, and a guided paranormal investigation inside one of the area’s most historically significant homes.
Taking place on Saturday, February 14, from 7:00 to 10:00 PM, the event offers couples a unique blend of romance, history, and mystery. Guests will enjoy a dessert-and-drinks reception before embarking on a two-hour paranormal investigation, led by a professional guide and supported with provided investigative equipment. No prior experience is required.
The Oliver Estate, located at 445 Plymouth Street, Middleborough, is deeply rooted in the region’s Revolutionary-era history and has borne witness to generations of life, change, and pivotal moments in the town’s past. Exploring the estate after hours offers guests a rare opportunity to connect with its rich historical legacy while experiencing the atmosphere of this remarkable property in a new and engaging way.
Tickets are $75 per couple and are limited to preserve the intimate nature of the event. Admission includes desserts, non-alcoholic drinks, use of paranormal investigation equipment, and expert guidance throughout the evening.
Tickets are available online at
DiscoverMiddleborough.Eventbrite.com
For additional information, please contact
discovermiddleborough@gmail.com
Official Site of
the Middleborough Tourism Committee
Christmas at the Oliver Estate: A Holiday Wonderland in Middleborough.
Middleborough, MA — The Middleborough Tourism Committee and Co-Host, May Flower Lodge A.F & A.M invites families and holiday enthusiasts to experience the magic of Christmas at the Oliver Estate, an enchanting celebration featuring seven acres of twinkling lights, festive music, and seasonal activities for all ages.
The event will take place on December 13, 14, 20, and 21 from 4:30 PM to 8:30 PM, transforming the historic Oliver Estate into a radiant winter wonderland filled with holiday cheer.
Visitors will delight in the Giant Christmas Village, Model Train displays, and a festive Christmas Market offering local crafts and gifts. Warm up with cocoa and cookies, enjoy visits with Santa, and explore free children’s activities designed to bring holiday joy to the whole family. Sparkling decorations across the estate’s seven-acre property promise to make this an unforgettable community event.
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Important Parking & Shuttle Information
There is no parking at the Oliver Estate.
All guests must park at Middleborough Town Hall (10 Nickerson Avenue).
A free door-to-door shuttle service will transport visitors directly from the Town Hall parking area to the estate and back throughout the evening.
Please plan to arrive early and enjoy the convenience of the continuous shuttle service — it’s part of the experience!
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Tickets are $5 per person and can be purchased in advance at Eventbrite.com. Children ages four and under are free.
“The Oliver Estate has always been a place where history and community come together,” said a spokesperson for the Middleborough Tourism Committee. “This year’s holiday celebration will continue that tradition by offering families a chance to make lasting memories in a magical setting.”
For more information, visit DiscoverMiddleborough.com, email DiscoverMiddleborough@eventbrite.com, or follow Discover Middleborough for updates.
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Event Details at a Glance
• Event: Christmas at the Oliver Estate
• Dates: December 13, 14, 20, & 21
• Time: 4:30 PM – 8:30 PM
• Location: The Oliver Estate, Middleborough, MA
• Parking: No on-site parking at the Oliver Estate
• Shuttle Pickup: Middleborough Town Hall, 10 Nickerson Avenue (Free shuttle service)
• Admission: $5 per person (children 4 and under free)
• Tickets: https://discovermiddleborough.eventbrite.com/
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About the Oliver Estate
Built in the 1700s by Judge Peter Oliver, the Oliver Estate is a cornerstone of Middleborough’s history. Once seized by the Sons of Liberty during the American Revolution, the estate now serves as a living museum and community gathering place for educational, cultural, and seasonal events that celebrate local heritage.
MIDDLEBOROUGH, MA – The Middleborough Tourism Committee invites the community to gather for the Annual Tree Lighting Celebration on Saturday, December 6, from 3:30 PM to 5:00 PM at Middleborough Town Hall, 10 Nickerson Avenue. This festive, family-friendly event is free and open to all. Visitors can enjoy live music, meet Santa, and participate in exciting door prizes and free giveaways — including a bike giveaway for lucky winners. The highlight of the evening, the Tree Lighting Ceremony, will take place at 5:00 PM sharp, illuminating the historic Town Hall in holiday cheer. Free parking will be available at the Town Hall for all attendees. Come celebrate the season with your friends and neighbors and make lasting memories in the heart of Middleborough! For more information, visit www.discovermiddleborough.com or follow @MiddleboroToday on Facebook. See less
𝐂𝐑𝐀𝐍𝐓𝐎𝐁𝐄𝐑𝐅𝐄𝐒𝐓 𝐈𝐒 𝐁𝐀𝐂𝐊
October 8, 2025 –The annual Crantoberfest celebration is set for Saturday, October 11, running from noon to 4 p.m. The festival will be held on the Town Hall lawn at 10 Nickerson Ave.
Crantoberfest features a full schedule of contests and events, including the following highlights:
• 1 p.m. – The Great Cranberry Bake-Off: Chefs and bakers are invited to compete for first, second, and third-place prizes in two categories: Professional and Home Baker. Winners will receive a gift card to Hannaford's and, naturally, bragging rights. Contestants must be sure to include a list of all ingredients with their entry.
• 2 p.m. – The Miss Crantoberfest Contest: Contestants will test their knowledge of the cranberry industry and showcase their Middleborough pride. The winner will be awarded a cranberry-colored crown and sash and will serve as a representative for the Tourism Committee throughout the year.
• 3 p.m. – The Annual Costume Parade: A highlight of the day! Children should come in costume to participate in the annual parade and enter to win prizes across two age groups: 8 years and younger and 9 years and older.
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Beyond the main stage events, attendees can explore dozens of vendors and food options. Adults can enjoy the beer garden hosted by the Bartending Service of New England while listening to festive German music.
Massachusetts Cranberries will be on hand with the travelling bog. It’s a great up close and person experience without getting wet.
Kids will have plenty to keep them entertained with activities like corn hole, exciting cranberry races, and the opportunity to take selfies with the alpacas.
For more information, please email HerringRunFestival@yahoo.com
Colonial Re-Enactment at the Historic Oliver Estate in Middleborough
• Date/Time: Sunday October 19, 2025 12:00 Pm to 4:00 PM
• Admission: FREE
• Parking: Free parking is available at Oliver Mill Park, Nemasket Street and Route 44, Middleborough, MA.
o Please note: there is no parking at the Oliver Estate. A convenient shuttle service will provide transport to the Estate.
Middleborough, MA – Step back in time and experience 18th-century life at the Historic Oliver Estate, 445 Plymouth Street, Middleborough, during a special Colonial Re-Enactment event. This family-friendly day of history and heritage is free and open to the public.
Visitors will enjoy an immersive colonial experience featuring:
• Colonial military drills and musket demonstrations
• Hands-on demonstrations in spinning, weaving, and cooking
• Farm animals and living history activities
• House tours of the historic Oliver Estate
• Children’s colonial-themed games and activities
• Access to 7 acres of colonial gardens
• Food and beverages available for purchase
Bring the whole family for an educational and entertaining day that celebrates colonial history and the role the Oliver Estate played in early America.
About the Oliver Estate:
Built in the 1700s by Judge Peter Oliver for his son and daughter-in-law, the Oliver Estate is one of Middleborough’s most treasured historic sites. The property’s deep ties to the American Revolution make it the perfect backdrop for a day of living history.
Media Contact:
Middleborough Tourism Committee
𝐆𝐇𝐎𝐒𝐓 𝐓𝐎𝐔𝐑 𝐓𝐈𝐂𝐊𝐄𝐓𝐒 𝐒𝐄𝐋𝐋𝐈𝐍𝐆 𝐅𝐀𝐒𝐓
October 8, 2025 – Ticket Alert: Don't miss your chance to step inside one of Middleborough's most haunted buildings this Halloween season.
Tours for the Town Hall Ghost Tour Investigation on October 17 and 25 are officially sold out. There are only a few tickets remaining for the tours on October 18 and 24.
Known for its legends and eerie history, the Middleborough Town Hall, 10 Nickerson Ave., is said to be one of the most haunted buildings in the area. This event offers a unique, 2-hour guided paranormal investigation after dark.
• Dates with Availability: October 18 and 24
• Tour Times: 6 p.m. and 9 p.m.
• Tickets: $20 per person
Led by professional ghost hunters, guests will use real paranormal investigation tools and equipment, such as EMF detectors, spirit boxes, and thermal cameras, to explore the building. As you move through the historic chambers, you’ll hear chilling accounts of unexplained activity and learn how investigators search for evidence of the supernatural. You'll even take part in experiments to detect possible spirit presence.
This immersive experience blends local history, storytelling, and hands-on investigation. Space is limited to keep the experience authentic and interactive, so gather your courage, bring your curiosity, and see if the Town Hall’s ghostly residents make themselves known.
Purchase Tickets at: DiscoverMiddleborough.eventbrite.com
#middleborough #ghosthunting
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Discover Middleboro
The Town of Middleborough is a 72.31 square mile historic industrial town on the Nemasket River. Incorporated in 1640, Middleborough is a unique blend of tradition and progress. Still a farming community, the town is known as the Cranberry Capital of the World. Although industry has increased greatly since the completion of Route 495, the community continues to embody pure “country” living with miles of green spaces, woodlands and rivers.
Visitors can enjoy several recreational activities including numerous sports programs, parades, and country fairs as well as venture through The Oliver Estate and Middleborough Historical Museum.
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