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'Obsessed' Nantucket traveler reveals where to go, what to do on the island in the fall
Nantucket Island has risen to popularity in the last few years thanks to popular books and shows portraying the quaint island.
A woman who’s been “obsessed” with visiting the vacation destination for more than 20 years shared some of her best kept tips and tricks to make the most of your time on the island.
“I have been going there since I was a baby, and then I started working out there at a restaurant during the summers in 2018, so seven summers ago,” Charlotte Drinkwater, a New York-based 23-year-old social media coordinator, told Fox News Digital in an on-camera interview.
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In a TikTok that has garnered over 3.7 million views, Drinkwater shows the beauty of the island — something she said that she and her family have been drawn to for years.
Charlotte Drinkwater (pictured here) has been visiting Nantucket in Massachusetts for more than 20 years. (Charlotte Drinkwater)
Drinkwater, who is originally from Massachusetts, said her parents met on the island “many, many years ago,” so it’s always held a special place in her heart as they would return each summer.
“We grew up vacationing on the island for usually like two weeks at a time, if not more, and then I think when I was in eighth grade… my family got a home there,” she said.
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Nantucket, Massachusetts, is roughly 105 square miles. (Charlotte Drinkwater)
She said, “It’s hard to ever be in a bad mood or have a bad time when you’re out there.”
Drinkwater explained that the island is special for many reasons — one of them being the community of people there that “take care of each other.”
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Drinkwater said that with family-owned restaurants and a lack of stoplights, the historic island is unique and makes “it feel like you’re in a different world.”
Drinkwater credits author Elin Hilderbrand, who is known to write novels about the island, for an increase in tourism over the last few years.
Drinkwater said one of her favorite things to do on Nantucket is eating meals on the beach. (Charlotte Drinkwater)
“She does a fantastic job at portraying the island. Especially after being in all of those places, [the books] really feel like you’re right there,” she said.
She added, “The lifestyle, the things people do and say, wear and act, are very to a tee accurate.”
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Some of her recommendations when visiting the island included eating dinner at Millie’s, enjoying a sandwich on the beach and visiting Cisco Brewers for live music and food trucks on the weekend.
Nantucket is located off the coast of Cape Cod, Massachusetts. (Charlotte Drinkwater)
Drinkwater recommended visiting all ends of the island — which is roughly 105 square miles in total, ranging 14 miles in length and three-and-a-half miles wide, according to the Nantucket, Massachusetts, government website.
“I would say if you’re visiting, don’t stay in one part of the island,” she encouraged, adding, “Try to get around as much as you can.”
The frequent visitor also cautioned visitors to beware of the peak tourism times on the island, specifically July and August, and to plan ahead when you can.
As for visiting Nantucket in the fall, Drinkwater said it’s a “perfect” time to see the island, with locals calling it “local summer” due to the lack of tourists.
A frequent visitor to Nantucket shared some of the best tips for enjoying your trip to the island. (Charlotte Drinkwater;iStock)
“It has the same beautiful weather as the summer, a little less hot, but minus the crowds, so you can go to the beaches and not have as many people there,” she said.
Drinkwater added, “I think, especially in October, seeing those orange leaves fall into the cobblestone streets is so magical.”
Drinkwater said that while fall is still a great time to visit, she recommends going on the weekend as some restaurants will close during the week to give their employees a break from the busy summer tourism rush.
Fall is also a common season for weddings to be held on the island.
“Definitely plan ahead for your dinners because there are not a lot of restaurants on the small island, so they do book up,” she said.
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The annual lottery is for standard white Massachusetts passenger license plates.
The Massachusetts Registry of Motor Vehicles announced on Monday it is now taking applications for the 2026 Annual Low Number Plate Lottery.
The annual lottery is for standard white Massachusetts passenger license plates. Winners and alternate winners will be selected using an electronic random number generator and notified by mail no later than Sept. 15.
To be eligible, an applicant must be a current Massachusetts resident with an active, state registered and insured passenger motor vehicle. They must also have a state-issued driver’s license or ID in good standing.
You can apply through Aug. 14 at the myRMV Online Service Center.
While there’s no cost to enter, “applicants selected in the lottery will be required to pay the special plate fee in addition to the applicable standard vehicle registration fee,” the RMV said.
Commercial vehicles and motorcycles will not be accepted as applicants. MassDOT workers and contract employees and their immediate family members are ineligible to participate, the RMV said.
PORTSMOUTH — Serving approximately 500 LGBTQ+ youth across the state, the nonprofit New Hampshire Outright has increased its programming by 25% over the past year.
Portsmouth Pride, the organization’s largest annual event, is set for Saturday, June 20, with roughly 5,000 people expected to attend the parade and events in the city throughout the weekend.
“We are serving more young people and families than ever before. Our impact is just growing day by day, year over year in terms of folks we’re able to serve and advocate for,” said Heidi Carrington Heath, NH Outright’s executive director.
The parade will step off at Pleasant Street around 12:30 p.m. Saturday, then loop through downtown to Strawbery Banke Museum, where the mainstage will host drag performances and musical acts from 1 to 5 p.m.
Heath, LGBTQ+ advocates oppose several bills before NH Gov. Kelly Ayotte
The moment is not without its challenges for the LGBTQ+ community. Heath pointed to three bills in the New Hampshire legislature that have her and other LGBTQ+ advocates around the state concerned.
The first, Senate Bill 552, awaits possible approval from New Hampshire Gov. Kelly Ayotte. The New Hampshire House of Representatives and Senate both approved the bill, sponsored by three Senate Republicans, which proposes to separate people by their biological sex in certain places, including bathrooms, locker rooms, involuntary detention facilities and sporting events.
Critics of the latest bathroom bill initiative oppose its implications for transgender youth and adults across the state, if it were to be signed into law by Ayotte. Both Ayotte and prior New Hampshire Gov. Chris Sununu vetoed restroom-focused bills in the past.
“We really pride ourselves on individuality and individual freedom,” Heath said. “I want us to return to those Granite State values in a variety of arenas. There is a very real cost to our kids to watching the people whose job it should be to protect you to debate your personhood in public.”
Ayotte faces another Republican bill – SB 430 – opposed by LGBTQ+ leaders in the state.
The bill, amended and adopted in both the state House and Senate, would require New Hampshire teachers and school employees to “honestly and completely” answer written requests from parents and legal guardians about their children.
The language of the bill does not directly address the LGBTQ+ community, but opponents worry that teachers may be forced to disclose a student’s gender identity or sexual orientation. If it becomes law, the mandate would take effect in New Hampshire’s schools Jan. 1.
“They just want to be kids,” Heath said of LGBTQ+ youth. “That is the gift of the work we do at New Hampshire Outright. We allow them to do that. They are navigating this in every arena of their life, out in their world, at school, etc. They just want to be kids. I want that for them, too. I really do.”
In addition, Republican Senate Bill 434, a book challenging measure, sits on Ayotte’s desk.
“No later than November 1, 2027, each local school board shall adopt a procedure to be used to address complaints submitted by parents or guardians alleging that material that is harmful to minors, age-inappropriate, or otherwise offensive or inappropriate for use in the child’s school,” the House and Senate-passed bill reads.
Complaints would be filed with the superintendent of a school district or a designee, per the bill.
What events are being held before and after Portsmouth Pride?
Before the Pride parade, from 10 a.m. to noon Saturday, attendees will be welcomed at the John Paul Jones House in Portsmouth to make flags and buttons for the event.
New this year, a ticketed New Hampshire Outright Pride after party with appetizers, drinks and dancing will be hosted by The Hawthorn, a Jewell Court events center, from 7 to 10 p.m. Saturday.
The weekend’s closing event — a ticketed drag brunch at the Music Hall Lounge in collaboration with Gather and New Hampshire Outright — will be held Sunday, June 21 at 10 a.m. The drag brunch is for ages 21 and older.
Ahead of Portsmouth Pride, Heath reported New Hampshire Outright has already led or assisted in organizing nine events this year throughout the New Hampshire and Maine Seacoast region.
“We are so excited about this weekend,” Heath said. “Pride is a protest. Pride is a celebration. We are just looking forward to welcoming the community to celebrate with us at Pride and showing up big, particularly for showing young people that their identity is their superpower.”
Want to get married? Ordained minister plans to marry LGBTQ+ couples after Portsmouth Pride
Rollinsford resident Jen Walton is the daughter of a gay woman. Throughout Walton’s upbringing, she experienced taunts and isolation at school as her mother hid parts of her identity from the public eye.
Some of Walton’s earliest memories are of attending Pride parades with her mother. Now an ordained minister, Walton plans to offer 10-minute wedding ceremonies following the Portsmouth Pride parade Saturday afternoon, an idea that took shape in recent days.
“I would love to just marry as many people as I can,” Walton said.
Walton, friend and fellow ordained minister Katie Brochu and friends will station themselves at the Prescott Park fountain Saturday afternoon following the Portsmouth Pride Parade.
Couples need to bring identification, a marriage license and $20 to be approved for an impromptu Pride park wedding, according to Walton.
Three different wedding ceremony styles will be offered to couples looking to tie the knot. Walton and her friends will be on hand from 1 to 5 p.m. as the Portsmouth Pride mainstage performances occur simultaneously nearby.
“We’re really all supposed to be in this together,” Walton said. “You learn from a very young age that people are individuals and not everybody is going to think, feel and believe the same thing. For me, it’s super important that I’m an ally. I’ve said it for years and years and I’ll say it for years and years, because it’s hard.”
The event is not sanctioned by New Hampshire Outright but has Heath’s and the organization’s full backing.
“It never ceases to amaze me and bring me joy the things that people want to do around Pride month,” Heath said.
All proceeds will be split evenly between New Hampshire Outright and the Trevor Project, an LGBTQ+ suicide prevention nonprofit.
From Camden and Cherry Hill to Trenton and the Jersey Shore, what about life in New Jersey do you want WHYY News to cover? Let us know.
The borough of Lawnside in Camden County will be honored with a historical marker from the New Jersey Historical Commission as part of the state’s Black Heritage Trail.
A ceremony unveiling the marker will take place at 10 a.m. Friday at Lawnside Borough Hall on Dr. Martin Luther King Jr. Road.
Marsharee Wright, aide to Lawnside Mayor Mary Ann Wardlow and long-time resident, said everyone is thrilled about the marker unveiling.
“We’ve invited the entire community and neighboring towns to come share the celebration with us,” Wright said.
Linda Shockley, president of the Lawnside Historical Society, said it’s “an extreme honor” for the borough to be included in the state’s program, especially as Lawnside is amid a year-long celebration of its centennial.
“It really lifts our profile and hopefully more people will understand and know what Lawnside is about and what it means in the nation,” Shockley said.
Lawnside was one of six sites selected in Camden County in 2024, including “The Point,” a historic Black neighborhood in Haddonfield. Its marker was unveiled last June.
During the ceremony, the borough’s history will be showcased, along with the original documents signed by Gov. A. Harry Moore in 1926, which made way for the borough’s creation.
Though there are many Black enclaves in South Jersey, the borough is the state’s only incorporated antebellum Black community. First known as Free Haven, and later Snow Hill, it was a stop on the Underground Railroad. Peter Mott built a three-floor dwelling in 1844 that was once part of sprawling farmland where he helped slaves escape.
Mott’s house, now owned by the Lawnside Historical Society, serves as an Underground Railroad museum.
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