🌷Plan a Shoulder Season Girls Trip to Martha’s Vineyard

Tips for small groups traveling April–May & September–October, plus a sample weekend itinerary

Jan 12, 2026

Martha’s Vineyard in peak summer is iconic, but shoulder season is when the Island becomes easy.

If you’re planning a girls weekend (friends, sisters, moms, milestone birthdays) and you want the scenery + charm without the crowds, long waits, and high-season pressure, April–May and September–October are the sweet spots.

This guide is designed for small groups (2–8 people) traveling for a quick weekend getaway (arriving Friday night and leaving Sunday afternoon) with most of the weekend spent in the down-island towns.

🌿 Why Shoulder Season Works So Well for a Girls Trip

Shoulder season is ideal for a girls trip because it’s the best of Martha’s Vineyard without the peak-summer chaos. There’s still plenty open, with enough restaurants and activities to fill a weekend without overplanning, but dinner plans are easier with less waiting. Lodging is also more available and often more affordable, so small groups can usually score better options, sometimes at much better rates than they’d find in the heart of summer.

This weekend style of trip is ideal for milestone birthdays, moms’ getaways or reset weekends, and friend groups who want food, shopping, and scenery rather than clubbing. It’s also perfect for repeat visitors who want a slower Vineyard vibe, and for first-timers who want the MV experience without the July and August intensity.

🗓️ When to Go: April–May vs September–October

🌷 April–May

The vibe: fresh start energy
Best for: cozy weekends, shopping + walking, calm meals out
Expect: more limited schedules, occasional windy days

🍂 September–October

The vibe: warm afternoons, true Vineyard beauty, Wedding season
Best for: warmer beach walks, fall decor
Expect: September is a little busier; October is cozier + earlier sunsets

🏡 Where to Stay

For a weekend trip, I’d recommend staying in one of the 3 down-island towns. Each has a different vibe, but they all make it easy to explore without needing a car.

⚓ Vineyard Haven (VH, Tisbury)
- Best for: easiest logistics + calm energy
- Memorable because: Easiest Steamship Authority arrival + departure, great for groups with staggered arrival times
- Hotels: Nobnocket, Mansion House
🎡 Oak Bluffs (OB)
- Best for: fun energy + classic Vineyard charm
- Memorable because: The most playful town (colorful, walkable, photo-friendly)
- Hotels: Summercamp, Oak Bluffs Inn, Morgan, AirBnBs walkable to Circuit Ave
⛵ Edgartown
- Best for: milestone weekends + elevated dinners
- Memorable because: Most polished “special occasion” feel, good shopping density, harbor strolls + lighthouse views
- Hotels: Harbor View, Faraway, HobKnob, The Edgartown Collection, AirBnB near Main Street.
🚗 Do you need a car?
- For this trip style: no. If your goal is to do half a day in each down-island town, a car is more hassle than help. You might want a car if: your group has mobility concerns, you’re staying far outside town, you want full up-island exploring (not the goal here)
- Shoulder season perk: if you do bring a car, ferry reservations are typically easier and cheaper than summer.

✅ What to Do (Shoulder Season-Friendly Picks)

Here’s what I would personally do with my friends!

🚶 Light adventure

State Beach walk (perfect shoulder season)
Oak Bluffs Ocean Park stroll
Edgartown Harbor + Lighthouse
Bike ride between OB ↔ Edgartown (if weather is nice)

🛍️ Shopping + browsing

Edgartown: best shopping + browsing (make this your “shopping half-day”)
Oak Bluffs: Circuit Ave stroll + casual browsing
Vineyard Haven: quieter shops + calmer pace (great for morning coffee and wandering)

🧘 Activities to Pre-Book

MV Picnics for custom bachelorette setups
Social Coast Mobile Bar for private mixology sessions
Stefanie Wolf Designs for in-store permanent bracelet appointments
Custom Tote Bags with Tote-Ally Yours
Erica Wilson for Private Needlepoint Lessons
Cooking Classes at Farm Institute
🔗 Yoga & Wellness Guide for top-rated instructors and spa options
🔗 Private Charters Boats to book for your group
🔗 Martha’s Vineyard Private Chef Guide to have a chef come to you

🏛️ Tourist-worthy / iconic must-sees

Gingerbread cottages (OB)
Edgartown lighthouse + harbor views

🍽️ Where to Eat & Drink (Shoulder Season Edition)

☕ Coffee / easy breakfast

Edgartown: Behind the Bookstore, Rosewater
Oak Bluffs: Aalia’s, Winston’s (takeout)
Vineyard Haven: Waterside, Art Cliff Diner (sit-down)

🥂 Dinner + Drinks

Walk-In:
- Oak Bluffs: Lookout Tavern, Nancy’s, Coop de Ville
- Edgartown: Seafood Shanty, Port Hunter
- Vineyard Haven: S+S Kitchenette, The Maker
With Reservations:
- Oak Bluffs: Sweet Life Cafe, Red Cat Kitchen
- Edgartown: The Covington, 19 Raw
- Vineyard Haven: 9 Craft Kitchen