The Ultimate Preppy Summer Getaway: Ugotta Regatta on Little Traverse Bay

The Ultimate Preppy Summer Getaway: Ugotta Regatta on Little Traverse Bay
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You may think of the preppy lifestyle as being a strictly southern affair. However, nestled deep in the MidWest, half way between the equator and north pole, is what may be one of the preppiest towns in the nation: Harbor Springs, Michigan. Step aside Nantucket, Harbor Springs boasts breathtaking lake views, cottages adorned with wrap around porches and American flags, and a host of preppy shops and restaurants. Take a stroll down Main Street, taste a classic Kilwin’s ice cream cone, or spend an afternoon on the pristine beaches of Lake Michigan and you will be taken back to the feel of classic American summer time. Take a sunset stroll through Wequetonsing, the epitome of a preppy neighborhood, and we guarantee you will never want to leave this beautiful lake town. 
Just when you thought this preppy oasis couldn’t get any better, late July rolls around, the sun shines high on the lake, and the Ugotta Regatta hosted by The Little Traverse Bay Yacht Club comes back for another year. Bringing sailboats from across the nation and flocks of eager visitors from the MidWest and beyond, this regatta is one of the greatest highlights of a Lake Michigan summer. It’s no wonder why so many adore this event, as it is the ideal depiction of the preppy coastal lifestyle. So preppy in fact, that Lilly Pulitzer named one of their most iconic prints “You Gotta Regatta,” after the event itself. The print has grown to be one of the company’s most popular, which comes as no surprise to those who know and love the Ugotta Regatta event.
 If you aren’t already convinced that you should see the Ugotta Regatta this summer for yourself, let us give you a run-down of the weekend and all of its fun family festivities. Whether you are racing your own boat (registration is first-come first-serve to boats over 22 feet) or just observing, this weekend is sure to be a great time. It all begins early in the morning on Friday of race weekend as eager visitors line up outside of The Irish Boat Shop, the areas local marina, to purchase the annual Ugotta Regatta tee shirt. A new design comes out each year, making the perfect addition to anyone’s preppy tee shirt collection. Once the tee shirts have been dispersed, you’ll spend the rest of the day soaking up sunshine by the lake, shopping downtown, visiting the open bar at Little Traverse Yacht Club (if you are a sailor or guest of one), or watching the one-design fleet race: the regattas smaller racing division. After the day’s fun festivities, it’s time to head home to get dressed for the Friday night “Welcome to Harbor Springs Party” hosted at The Irish Boat Shop. A casual and fun affair, you’ll mingle with sailors and fellow observers eager for the weekend’s races as you sip, snack, and take in the sunset views. Afterwards it’s time for some shut eye...Saturday will be a big day!
 Saturday starts with a 7:30am pancake breakfast open to the public at Little Traverse Yacht Club, where sailors and observers can fuel up for the big day ahead. Once the horn blows at noon, the race is on! Unless you race yourself, the best location for watching the regatta is either on a power boat in the midst of the lake, or from The Petoskey State Park, a mere 10 minute drive away. Nothing quite beats the thrill of cheering these sailors on as their boats rush across the sparkling blue waters of the lake. A simple American lake tradition that you and your kids will remember and cherish for a lifetime. At 4pm the races are finished for the day and it’s time to celebrate! The Saturday evening Ugotta Regatta party hosted at The Little Traverse Yacht Club is a vibrant and preppy affair filled with sauvignon blanc, seersucker, and celebratory sailors. While this party is open only to those who participated in the race itself, there is no reason you couldn’t host your own après sail soirée the same evening.
 The sun rises on Sunday morning and it is time to repeat yesterday’s activities. Once again pancakes are served bright and early at Little Traverse Yacht Club and the regatta proceeds upon the sounding of the horn at noon. For a change of scenery today, view the race from the Petoskey Sunset Park. As the race day comes to an end, everyone feels bittersweet knowing their favorite summer event has come to a close. If you or your friends or family sailed in the regatta, however, you still have one last hurrah before the weekend is over. The awards ceremony for racers and their family and friends held at The Little Traverse Yacht Club is a festive way to close out a weekend of sailing while, celebrating those who ranked highly in the races. Monday morning, as you turn on to M119 and head for home, you’ll be sad to see this beautiful town growing smaller and smaller in the rear-view mirror, but excited for next summer when you get to do it all over again.
By now we hope you are thoroughly convinced that The Ugotta Regatta should be on your summer bucket list this year. July 26th will be here faster than you think, so we have collected all the essentials you’ll need in order to have you looking your preppy best throughout all the regatta weekend events.

For the lake

You’ll be spending a lot of time in or around the water over regatta weekend, so swimwear and water resistant clothes are a must! From beach time on the lake, to splashing around in a boat, to racing in the regatta itself, we have all the apparel to keep you comfortable and stylish.
Ladies, may we suggest:

Perfect to throw on when cruising around the lake on a boat! It may be late July but the north Michigan breeze can get a bit chilly early in the morning and late in the evening. This jacket will keep you dry and warm for all your lake adventures over regatta weekend.

The Gingham Brighton Short by Southern Marsh, $49.

Need an easy cover up when transitioning from bar to boat to beach over regatta weekend? Look no further than these vibrant gingham shorts that pair well with a swimsuit and sandals

Fellas, may we suggest:
The perfect shorts for sailing in the regatta don’t exist…said anyone who hasn’t yet laid eyes on these beauties. The retro vibe of these shorts will pair excellently with your new Ugotta Regatta tee shirt.
A shirt we guarantee you’ll wear all regatta weekend long! Performance material will keep you cool and dry in and out of the lake, while the classic strip and preppy look of the polo will keep you looking classy.

For the Yacht Club parties

Ladies, may we suggest:
The Little Traverse Yacht Club parties on Saturday and Sunday night are your opportunity of the weekend to get dressed in your preppy best! Whether you are attending these parties or hosting your own, this dress is sure to make you the style icon of the party.
Seersucker is the preppy gals go to party dress, perfect for any classy party you’ll attend over Ugotta Regatta weekend. We can already picture you in this dress with a pair of Jack Rogers and a pearl necklace.
Fellas, may we suggest:
Walk into a regatta party wearing these bright madras pants and you’ll be the talk of the town, in the best way possible. Who doesn’t love a preppy man in madras pants and boat shoes?
Ahh, the classic preppy party outfit: a VV plaid button down, khakis, and Sperry’s. Now just picture yourself in that outfit amidst a Ugotta Regatta weekend party. Have you clicked “add to cart” yet?

For the casual parties + evenings in Harbor Springs

Ladies, may we suggest:

V-Neck Shaker Sweater by 525 America, $88.

Perfect to throw on with jeans or shorts and casual shoes for the Irish Boat Party cookout or for an evening with your family in Harbor Springs. Soft and warm, you’ll reach for this sweater all weekend after your hours spent in the sun.

The Sarah Skort by Southern Proper, $44.99

The perfect outfit for strolling down Main Street in between the races, perhaps stopping for an ice cream and visiting the local small businesses for some shopping. Comfortable as a pair of shorts (well because they are) with all the fashion of a pleated skirt, this skort will keep you looking and feeling your best for all your regatta weekend festivities.

Fellas, may we suggest:

Long sleeve Half Dome Tee Shirt by The North Face, $30.

For your casual events over Ugotta Regatta weekend, you’ll need a great preppy tee shirt. This long sleeve from The North Face is a great basic for wherever the weekend may take you. Throw it on with your swim trunks after a day on the lake and you’ll be ready for wherever the evening takes you.

Stretch Seersucker Short by Southern Tide, $89.50

Everyone loves a man in seersucker, especially on Ugotta Regatta weekend. Wear these shorts from a boat ride, to a casual dinner in town or the regatta cookout and you’ll be on the cloud 9 of preppy style.


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  • Author image
    Wahoowah81: August 07, 2019

    Allison. Wonderful article. I’ve added Harbor Springs to my bucket list of places to visit. 😎

  • Author image
    Joy: July 29, 2019

    Love the blog, and so well written! Thank you for sharing.

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