Movies like Pumpkin Regatta Romance (2026)
The best movies like Pumpkin Regatta Romance (2026) are Love on Harbor Island (2020), Surprised by Love (2015) and The Enchanted Christmas Cake (2021). If Pumpkin Regatta Romance hooked you with its romance and tv movie, these 20 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedWhat's Love Got to Do with It? (2023)6.1/10 from 253 votes
- NewestProm Pact (2023)Released 2023
Love on Harbor Island (2020)
Interior designer Lily returns home to help her Aunt Maggie run her marina-side bed and breakfast when she meets Marcus, a handsome seaplane pilot whose work delivering rescue dogs helps Lily discover that home really is where the heart is
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisSurprised by Love (2015)
The story of a young businesswoman who tries to convince her uptight parents to accept her current boyfriend and instead finds herself falling for an old high school flame.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisThe Enchanted Christmas Cake (2021)
Gwen recently lose her grandmother and she is struggling to run their bakery and regain the Christmas spirit, and figure out her grandmother's magical recipe for the town's legendary Enchanted Christmas Cake.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisA Merry Christmas Wish (2022)
Janie, a rising marketing executive living in The Big Apple, returns to her hometown of Woodland Falls when her Great-Uncle Randall passes away. Randall has even arranged for his farmhand, Dylan to help at the event, which is being held in the farm’s sprawling barn. Aware that her Manhattan boyfriend is anxious for her to return to the city so the pair can jet off to a previously planned holiday on the beach, Janie begins to feel an unexpected emotional tug about living life in a more authentic, meaningful way.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisSame Time Next Week (2017)
Sara deals with her grief by trying to complete her late husband’s bucket list. Injuring herself on one of the tasks leads her to meet Dr. Ryan. A widower himself, Ryan begins to help Sara complete the bucket list. The two get close and Sara doesn’t want to betray her husband’s memory, so she stops seeing Ryan. However, Ryan doesn’t give up and helps Sara realize that everyone deserves a second chance at love
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisAs Luck Would Have It (2021)
When Lindsey travels to Ireland to acquire land that is perfect for a resort, she decides to enter the town's matchmaking festival to prove her investment—and win over a handsome local.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisChristmas at the Drive-In (2022)
Sadie Walker is starting over in her hometown of Chesterfield, New York, following a series of major life disruptions that include leaving her law practice after losing her biggest case and no longer being engaged.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisMarrying Mr. Darcy (2018)
Schoolteacher Elizabeth Scott and businessman/philanthropist Donovan Darcy are blissfully in love and newly engaged. As the weeks fly by and the arrangements for their small autumn wedding grow more elaborate and Donovan, wrapped up in his work, is increasingly unavailable. Reminded yet again of their tremendous differences in background and temperament, Elizabeth can’t help but ask herself: should she marry Mr. Darcy?
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisA Cookie Cutter Christmas (2014)
Two longtime rivals and elementary school teachers duke it out during the holidays in a Christmas cookie bake-off, but their real feud ignites over a shared interest in a handsome single dad. With both determined to win the prize and the romance, their competitiveness could jeopardize what matters most this Christmas season.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisSister of the Bride (2019)
After only 6 months of dating, Stephanie and Ben get engaged and are delighted to share the news. However, they hit a road bump when Stephanie’s parents show concern that the couple has moved too fast.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisCatering Christmas (2022)
A fledgling caterer, Molly Frost, is hired by Jean Harrison, the perfectionistic director of the renowned Harrison Foundation, to cater this year’s annual Christmas Gala dinner. Things get complicated when Molly falls for Jean’s nephew, Carson, 30s, a travel photographer with no desire to take over the family’s foundation… until his aunt assigns him to the task of making sure the catered dinner goes perfectly.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisHer Pen Pal (2021)
Event planner Victoria can’t wait to attend –- and plan –- her best friend’s wedding in Paris. But when she finds out her ex is bringing a date, Victoria reconnects with her French childhood pen pal.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisA Christmas Miracle for Daisy (2021)
Whitney Alder owns interior design firm Marietta Designs, which she runs with her friend Andi in the small town of Marietta, Montana. Whitney is designing Santa’s float for the annual Marietta Christmas Parade when a potential job opportunity comes her way: the full redesign of a landmark home by Christmas Eve.
Why it matches: Recommended by TMDB viewers · both romance & comedy
SnoozefestMovies like thisProm Pact (2023)
It's prom season, and high school senior Mandy and her best friend and fellow outsider Ben are surrounded by over-the-top "promposals." Mandy is only focused on getting into her dream school Harvard, but as she starts tutoring basketball all-star Graham, she must re-evaluate whether her dream school is worth the cost of everything she believes in.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisNearlyweds (2013)
Revolves around three friends who have dream weddings only to find out that the pastor who married them failed to complete the key paperwork required to make them official.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisLove Under the Stars (2015)
Young at heart graduate student Becca strikes up an unlikely friendship with Emily, a quiet girl who recently lost her mother. With every passing play date chaperoned by Emily's father, Becca helps Emily come out of her shell and cope with her loss, and Emily teaches Becca to take on adult responsibilities. When a romance develops between Becca and Nate, though, the two must learn to balance their new relationship with Nate's responsibility to Emily, and with Becca's responsibility to finish her education.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisAll for Love (2017)
When a romance novelist is teamed with a Navy SEAL as research for her book, by a mandate from her publisher, she is less than thrilled and he is more than honest. However, as she works with the SEAL, she has a change of heart and learns to look at her life and writing with a different point of view.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisWhat's Love Got to Do with It? (2023)
Two childhood friends now in their thirties must decide whether to follow their heads or their hearts once the man decides to follow his parents' advice and enter into an arranged marriage in Pakistan.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisSailing Into Love (2019)
A biology teacher’s crusade to save a nearby island from development leads to unexpected romance with the handsome and mysterious young sea captain who is new to the seaside town of Willow Bay.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisClear History (2013)
Nathan Flomm, in order to avoid the humiliation of having missed out on a hugely successful business, assumes a new identity on Martha's Vineyard. He plots revenge when his former business partner moves to the same town.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like this
Like Pumpkin Regatta Romance and something else?
Blend two favourites and we’ll find the films in between.
Frequently asked questions
What are the best movies like Pumpkin Regatta Romance?
The closest matches to Pumpkin Regatta Romance are Love on Harbor Island (2020), Surprised by Love (2015) and The Enchanted Christmas Cake (2021). Below are 17 more, each with the reason it matches.
What should I watch after Pumpkin Regatta Romance?
Start with Love on Harbor Island (2020), the closest match to Pumpkin Regatta Romance.
What is the highest-rated movie like Pumpkin Regatta Romance?
What's Love Got to Do with It? (2023), rated 6.1/10 by 253 TMDB users.
What is the newest movie like Pumpkin Regatta Romance?
Prom Pact (2023) is the most recent release on this list.
Are there English movies like Pumpkin Regatta Romance?
Yes: Love on Harbor Island (2020), Surprised by Love (2015) and The Enchanted Christmas Cake (2021).
How are movies similar to Pumpkin Regatta Romance chosen?
First come films that Trakt’s viewers watch alongside Pumpkin Regatta Romance, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.