Up North Guide · Traverse City and the Leelanau Peninsula
The Perfect
Long Weekend.
Three Days. No Filler.
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Up North Guide · Traverse City and the Leelanau Peninsula
The Itinerary
Day 1 — Friday
A half day in Traverse City — low key by design.
Settle In
Get to your accommodation, and if you're feeling adventurous, unpack.
Front Street
Walk the three-block stretch of Front Street between Boardman and Union. This is the heart of downtown TC — Victorian storefronts, independent boutiques, galleries, a few good coffee shops. It's walkable, unhurried, and the best possible introduction to the town. Pick up something local to take home while you're at it.
Parking is tight on Front Street itself. If you can't find a spot, try the side streets.
Dinner
Poppycocks at 128 E. Front — TC's best all-around dinner, open since 1989, live jazz on Fridays, creative New American menu. Reservations strongly recommended on a Friday night. Alternatively, walk to The Little Fleet on 448 E. Front for something more casual: rotating food trucks, craft beer, outdoor seating, live music, and no reservation needed.
If Poppycocks is fully booked, The Little Fleet is genuinely great and zero stress.
Nightcap
If you're in the mood for a drink before heading home, The Parlor at 205 Lake Ave for a cocktail in a converted 1800s cherry warehouse with live music — opened December 5, 2013, exactly 80 years after Prohibition ended. Or head downstairs to Low Bar, in the basement of 7 Monks on Union Street, for 70+ whiskeys and serious pre-Prohibition cocktails in a candlelit speakeasy. Low Bar is closed Sundays, so tonight is your shot.
Day 2 — Saturday
Go early. Earn your lunch.
Coffee and Light Breakfast at The Mill
If you want coffee and something light before starting the hike, The Mill in Glen Arbor opens early — excellent coffee, fresh-baked pastries, and a sunny patio right on the Crystal River. It's en route to the dunes and a beautiful way to start. Skip it if you want to hit the dunes first thing.
The Mill's cafe is more casual than Supper (their dinner). Just walk in.
Morning: Sleeping Bear Dune Climb
Get there before 10am — the dunes are brutal in midday summer heat and significantly more crowded. The first dune is a 10-minute climb and completely worth it for the view of Glen Lake appearing suddenly below you. The full hike to Lake Michigan is 3.5 miles round trip over open sand: harder than it looks, further than it appears, and one of the most memorable things you can do in Michigan. Decide before you start how far you're going.
Make sure to bring water!
Lunch: Art's Tavern
You've earned it. Art's has been at the corner of M-22 and Lake Street in Glen Arbor since 1934. The burger is the thing to get, and has been since the beginning. College pennants cover the ceiling, a jukebox sits in the corner, and old photos line the walls. A necessary lunch stop to get the feel of Glen Arbor.
Cash or check only. There's an ATM on site.
Afternoon: Glen Arbor & Cherry Republic
Walk off lunch in Glen Arbor. Cherry Republic is the definitive stop: 200+ cherry products to sample freely, a winery with complimentary tastings, the Cherry Public House with 12 craft beers on tap, and homemade cherry ice cream. Browse the town's small galleries and shops at whatever pace feels right.
Evening: Choose Your Direction
Two good options depending on your mood and whether you scored Mill dinner reservations.
Day 3 — Sunday
Small towns and a hike — or a full day on the wine trail.
Option A · Small Towns + Nature
Morning: Pyramid Point
A 2.7-mile loop through old beech-maple forest to a 300-foot bluff overlooking Lake Michigan and both Manitou Islands — the best view-per-effort ratio in the entire park, and almost always quiet. The overlook is only 0.6 miles from the trailhead. Go in the morning before the temperature climbs.
Midday: Fishtown, Leland
Carlson's Fishery has been smoking fish off the same dock for three generations. The Village Cheese Shanty is right there. Van's Beach is a five-minute walk. The Manitou Island ferry departs from the Fishtown dock if you want to extend the adventure.
Afternoon: Suttons Bay
Wind back toward TC along the eastern shore. Suttons Bay is the most underrated town on the peninsula: walkable downtown, independent shops, the Bay Theatre (a 1946 community-saved movie house), and Hop Lot Brewing just south on M-22 — one of the best beer gardens in the region. Dogs and families welcome.
Option B · Winery Trail Day
Breakfast: Downtown TC
The Burrow TC at Grand Traverse Commons is consistently called the best brunch in TC — order the cinnamon roll. Or Archie's Social House downtown for a boho-chic start with locally sourced eggs and excellent coffee. The Burrow can have a wait on Sunday mornings, so get there by 9am or plan accordingly.
Book a Guide — Don't Drive Yourself
Magic Shuttle Bus and Traverse City Wine & Beer Tours both run Old Mission Peninsula routes with knowledgeable guides — one van, five wineries, everyone drinks freely. Book well in advance, as summer weekends fill fast. Check with your accommodation hosts if they partner with either tour.
The Route: Old Mission Peninsula, South to North
Chateau Chantal (terrace overlooking both bays, acclaimed Riesling), Mari Vineyards (estate Italian varietals, small plates, beautiful views), Brys Estate (the Frosé, the Tasting Tower), Hawthorne Vineyards (outstanding Gewürztraminer — the best wine in Michigan), and Bonobo Winery (northernmost stop, keep every branded glass you drink from). Bonobo has a secret rye whiskey for those who know to ask for it.
Evening: Dinner + Sunset in TC — Either Way
Head back to Traverse City for your last dinner up north. Pepenero at the Village at Grand Traverse Commons for elegant Sicilian pasta in a former 19th-century hospital chapel, or Poppycocks on Front Street if you didn't get there on Friday. If you want a livelier sendoff, try hitting up Two Sons for some great pizza and pinball. Either way, make sure you're somewhere with a view of West Bay at sunset — it starts around 8:30pm in summer, so time dinner accordingly. Clinch Park Beach faces due west — walk down after dinner and just sit by the water. That's your last image of the weekend. Or, if you want another winery, the sunset from Rove Winery is something else entirely — 1,165 feet up, views over the whole Leelanau, and a glass of something good in your hand.
Where We Recommend Staying
Streamside sits at the heart of the Leelanau Peninsula — a short drive from downtown Traverse City and Front Street, and equally close to the Sleeping Bear Dunes and Glen Arbor. Everything on this itinerary is within easy reach.
A private hot tub and barrel sauna waiting when you get back. A stream running through the property. Three bedrooms for the group. This is the one.
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